Career & Business Coaching Blog for Creatives & Entrepreneurs.
Inspiration, guidance, and practical strategies for multi-passionate professionals who refuse to choose just one thing.
Complete Portfolio Career Guide: Design a Professional Life That Fits You
A portfolio career (or polygamous career, as I have heard it being called lately) is a thoughtfully designed professional lifestyle that combines multiple income streams, rather than relying on a single full-time job. For creative generalists who notoriously resist specialization, this approach allows you to pursue multiple passions simultaneously while building financial stability and freedom. Here is everything you need to know to build yours.
This guide is designed for multi-passionate professionals, multipotentialites, and "scanners/slashers" who feel constrained by traditional career paths.
What you will learn:
The 5 specific models I use in my own portfolio career and with clients to help them structure a successful portfolio career.
A proven 5-step framework to transition without financial recklessness.
How to find the "glue" that connects your seemingly random interests.
As a career coach for creative generalists, I have helped hundreds of clients move from feeling "scattered" to building profitable, sustainable careers that honor their many interests and passions.
What Is a Portfolio Career?
A portfolio career intentionally combines multiple income streams. It's not juggling random gigs or endlessly trying to make ends meet, but a thoughtfully designed collection of 2-5 roles that create financial stability and fulfillment.
Unlike a chaotic "side hustle" life where you are reacting to financial panic, a portfolio career is something you build. You choose the pieces. You design how they fit together. You decide when to scale one up or down.
This path is best suited for creative generalists, multipotentialites, and polymaths: people who have a wide range of interests across seemingly unrelated domains and experience boredom in single-track roles.
Why is this career path exploding right now?
The Normalization of the Gig Economy: By 2027, freelance and contract work is projected to make up the majority of the US workforce. The infrastructure to support multiple income streams has never been better.
AI and Automation: As AI handles specialized, repetitive tasks, the ability to connect dots across different fields (a core generalist skill) is becoming a premium asset.
The Craving for Autonomy: More people are opting out of the "golden handcuffs" of corporate life in favor of ownership and autonomy. I see it in my coaching practice every day. A portfolio career offers diversification; if one income stream isn't working out, you have others to lean on.
Key takeaway: This is about intentional design. You are building a diversified investment portfolio, but instead of stocks, you are investing in your skills.
Is a Portfolio Career Right for You? 10 Signs
You are likely a good fit for a portfolio career if these 10 traits resonate with you:
You have multiple passions you refuse to give up. The idea of "picking one thing" feels like a physical loss to you. As soon as you have made a decision, a sense of panic sets in about all the doors you are closing. If this is you, I see you.
Boredom hits fast. You master the 80% of a job quickly, and once the learning curve flattens, you are ready to quit. Now that you've learned what you came to learn, the 20% left feels like useless repetition.
You've been called "scattered," but that's not you; you just have a lot of energy for different things. You NEED variety as much as you need oxygen.
You are a quick learner. You can dive into a new domain and become proficient faster than most specialists. This means that when something is hard, it's not always easy for you to stick with it.
Standard job descriptions feel suffocating. You often feel compelled to cut off parts of yourself to fit into a professional box. You feel undervalued and your talents underutilised.
You see eclectic connections everywhere. You naturally apply insights from one field (such as gardening) to a completely different one (such as software design). You have gut feelings about people you need to introduce to one another, and you map thoughts and ideas over unrelated disciplines.
Your resume is "unconventional" to say the least. You have multiple career changes or major shifts in your history. You feel you didn't "choose" your career; it was luck and other people.
Variety energizes you. Switching tasks doesn't drain you; it actually wakes your brain up. You might have been told that you switch too much and too quickly between jobs or subjects.
It is hard to explain what you do. When people ask at dinner parties, you hesitate or give a different answer every time. Or you overwhelm them with everything you are and do, because you don't want to leave anything out.
You believe diversity is an asset. You know deep down that your range is a superpower, not a liability. You just don't know how to make it work in your favor.
If 7 or more of these resonate, a portfolio career likely fits your unique nature.
Reframing the "Jack of All Trades"
Society often shames generalists with the quote "Jack of all trades, master of none." But the full quote is actually: "A jack of all trades is a master of none, but oftentimes better than a master of one."
History is full of successful portfolio careerists. Leonardo da Vinci wasn't just a painter; he was an engineer, anatomist, and architect. Benjamin Franklin was a writer, diplomat, scientist, and inventor.
Another remarkable generalist from history is Hedy Lamarr, a Hollywood actress and inventor. While celebrated for her on-screen performances, she also co-developed a frequency-hopping communication system during World War II, laying the groundwork for modern technologies such as Wi-Fi and Bluetooth.
What I like about Lamarr's story is that her pursuit of multiple passions is a great example of how our generalist interests drive groundbreaking innovation and lasting impact.
What all of these generalists have in common? They didn't succeed despite their wide array of interests; they succeeded because of it. You're in good company.
Take the Creative Generalist Quiz
5 Portfolio Career Models
Based on my work with generalists over a decade and my own varied career, I've identified 5 core portfolio career structures. You'll probably shift between these over time, so treat them as flexible starting points, not fixed labels. Also, choose the model that best fits your financial needs, risk tolerance, and, most importantly, your primary professional goals. You can always change your mind later (yes, truly!).
1. Main & Sides (The Conductor)
Structure: One core job or contract covers most expenses; 1–3 "sides" provide creative outlets and secondary income (typically 60–90% of the main, with the rest from the sides).
Best for: Anyone who values security but craves creative variety. Great for those with financial obligations, people starting their multi-passionate journey, or anyone needing a predictable paycheck.
Income Timeline: The main provides immediate, consistent income. Sides may take 6–12 months to grow, but there’s no pressure for them to "match" your main source.
Time Management: The main dictates most of your schedule (e.g., a 9–5). Sides slot into weekends, evenings, or blocked days off. Requires strong boundaries to protect creative time.
Pros: High stability. Low risk. Lets you experiment and build skills safely. Clear professional identity.
Cons: Can feel like working two jobs. Burnout is possible if you don’t protect your time fiercely. Sides may struggle for your attention or feel less “serious.”
First Steps: Secure or optimize your main. Choose just one side to start. Block out 3–5 hours weekly - non-negotiable - for that project.
2. Equal Parts (The Tightrope Walker)
Structure: Multiple (typically 2–3) core income streams, each at 30–50% of your income/time.
Best for: Thrives on variety and context-switching. Skilled at juggling. Ideal for those wanting to be fully multi-passionate in their work.
Income Timeline: Takes time, often 1–2 years, to build multiple stable streams. Many start with the Main & Sides model, then grow a side into a second (or third) main.
Time Management: You control your schedule: theme days, split days, or even alternating weeks. Requires strong organizational systems.
Pros: Highly diversified risk. Maximum variety. True freedom to explore multiple talents.
Cons: Hard to explain to others. Risk of looking “scattered.” Must market/manage several streams at once.
First Steps: Identify your top 2–3 interests with earning potential. Build one for stability, then layer in the next. Craft a simple message that connects your slashes.
3. Seasonal Rotation (The Choreographer)
Structure: Distinct “seasons” (e.g., Q1–Q2 for one focus; Q3 for another; Q4 for downtime or planning).
Best for: Those who value immersive focus, avoid context switching, or whose work aligns with seasonal demand (tourism, teaching, tax preparation).
Income Timeline: Often “lumpy.” You might earn 80% of your annual income in half the year, so saving for leaner months is key.
Time Management: You sprint, then rest. Your year is planned in blocks, not weeks.
Pros: Lets you go deep. True work-life balance (real downtime!).
Cons: Income/energy swings. Needs rigorous financial planning and self-awareness.
First Steps: Map your year by energy, season, or opportunity. Budget to smooth out lean periods.
4. Passion + Good Enough Job (The Patron)
Structure: Income: 80–90% from job; Fulfillment: 80–90% from passion.
Best for: Artists, musicians, or anyone building a creative pursuit that isn’t yet profitable, but refuses to give up on it.
Income Timeline: The job delivers steady income. The passion side may or may not ramp up financially over time, and that’s okay.
Time Management: The job is stable and contained (ideally not mentally draining). Reserve your creative or energetic hours (evenings, mornings, weekends) for what really lights you up.
Pros: Freedom to build your dream without financial panic. Job doesn’t define you, your passion does.
Cons: Passion side can feel “less real” if not making money yet. Risk of job draining your time/energy if not chosen carefully.
First Steps: Find a day job that leaves you with energy and isn’t toxic. Give your passion protected time every week, no guilt.
5. Exit Plan (The Grand Finale)
Structure: Starts with 90% of income/time in your current job and 10% in your new passion/project. Gradually shifts, over months or a couple of years, until you reach 0% traditional, 100% new.
Best for: Anyone ready to leap but needing a proof of concept before going all in. Great for corporate careerists, midlife shifters, or side-hustlers planning their exit.
Income Timeline: The “exit” can take 1–3 years, depending on your savings, risk, and how your passion side grows.
Time Management: Balance your “main” for security and allocate protected time for building the new thing. Eventually, scale back the old as the new ramps up.
Pros: Lower risk than a cold-turkey exit. Time to test, learn, and fail before fully committing.
Cons: Splits your focus; takes patience and discipline.
First Steps: Set clear milestones to move from 90/10 to 50/50, then to 0/100. Celebrate each step forward.
These models are the ones I have seen repeatedly in my work and in my own professional life. However, they are just launchpads. Start where you are, and evolve as you grow. Only you know what kind of portfolio career will work for you, and that is precisely the point!
Download the free Portfolio Starter Kit if you want to dive deeper
5-Step Framework to Design a Sustainable Portfolio Career
Here is the proven framework I use with clients to help them get started with sustainable portfolio careers that don't lead to burnout.
Step 1: Audit Your Interests
Before you strategize, you must see the full picture. List everything you love, everything you are good at, and everything you are curious about. Don't edit yet. Include professional skills (coding, writing) and "hobbies" (baking, interior design). Look for patterns. Often, the things we dismiss as hobbies are actually viable income streams waiting to be packaged correctly.
Step 2: Find Your "Glue"
This is the most critical step for positioning. What connects your many interests? If you're a coder who loves baking, your glue might be "systems." If you're a writer who loves therapy, your glue might be "narrative healing." It's the best starting point. It explains why you do these different things.
Step 3: Test Market Demand
Now, validate. Which of your interests are actually monetizable? Look at job boards, freelance platforms like Upwork, and competitor pricing. Where does your passion intersect with market need? You're looking for evidence that people are already paying for the solution you want to provide. Don't guess, research.
Step 4: Choose Your Model
Pick one of the 5 models above based on your reality today. Do you have six months of savings? Maybe you can risk the Equal Parts model. Do you have a mortgage and kids? The Main & Sides model is likely your best starting point. Be honest about your risk tolerance. An anxious nervous system kills creativity. Choose the structure that makes you feel safe enough to experiment.
Step 5: Build Incrementally
The biggest mistake creative generalists make is launching three new income streams on Monday. Don't do this. Start with ONE new stream while keeping your current stability. Get that first stream to a "minimum viable income" level before adding the next. A sustainable portfolio career is built over 6–18 months, not two weeks. Most successful portfolios evolve through intentional job design; they don't appear overnight.
[Internal Link: Need help designing yours? Check out my Coaching Services]
A portfolio career is the ultimate act of self-acceptance for the creative generalist. It stops the war within yourself, the part that wants safety vs. the part that wants adventure, and gives both a place to live. By choosing one of the 5 models and building incrementally, you can create a work life that honors your complexity instead of suppressing it.
You don't have to choose "one thing." You just have to choose how to fit them together.
Ready to design your unique portfolio career?
As a multi-passionate, it can often feel like you are constantly being told to "just pick one thing." But what if I told you that you don't have to choose just one passion or career path?
In fact, by embracing your interests and combining your passions in a unique way, you can create a fulfilling and financially stable career that allows you to thrive. Don't let society pressure you to hold you back from pursuing all of your passions.
Frequently Asked Questions About Portfolio Careers for Creatives
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Not if your positioning is clear. If you present yourself as "I do X, and Y, and Z," you confuse people. If you lead with your "glue," the value that connects them, you look versatile, not scattered. For example: "I help brands communicate better through design (Service A) and copy (Service B)."
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Only if you don't set boundaries. A portfolio career requires strict time management. You must be the boss who says "no" to yourself. In my work with clients and my own career, I use systems like time blocking and "theme days" to make sure you are fully present in whatever role you are playing that day. Without systems, you don't have a portfolio; you have a mess.
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Yes, often more than a traditional career. By diversifying, you create multiple revenue streams and are less vulnerable to a single layoff. Many generalists find that combining high-value consulting with scalable products (like courses) raises their income ceiling significantly.
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Typically, 6 to 18 months to fully stabilize a new portfolio structure. It depends on your existing network, your financial runway, and how aggressively you build your new streams.
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Absolutely not. In fact, I rarely recommend it. The Main & Sides model allows you to test your new income streams while still getting a paycheck. Quitting without validation puts unnecessary pressure on your creativity.
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No. You can have a part-time employment contract (W2) as one "slice" of your portfolio pie, combined with freelance work, passive income, a small business or even creative projects. You decide how you structure your career!
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That's the beauty of a portfolio career, it's changeable and modular. If one stream isn't working or bores you, you can swap it out without losing your entire livelihood. You are building a flexible ecosystem, not a rigid prison.
Career Coaching for Creative Generalists: How to Get Unstuck and End the Overthinking Cycle
If you identify as a creative generalist, a t-shaped, multi-hyphenate, multi-passionate creative, or an ambitious doer, you know this frustrating cycle well: you’re full of ideas and capabilities, and still you feel so agonisingly stuck. Instead of building an inspiring career (or boldly pursuing that long-overdue career change), you’re caught in a loop of endless overthinking and anxiety.
This challenge is precisely why I became a coach, and why specialized career coaching for creatives navigating a career change is so effective. The goal is simple, but life-changing: to help you finally work on your goals instead of just thinking about them, especially if those goals include pivoting to a more fulfilling professional life.
The Creative Generalist’s Unique Mental Blocks
Creative generalists operate differently; they are the broad thinkers in a world that still values specialization. They have a non-linear, sometimes accidental career history (often called a portfolio career) and possess qualities like compassion, ambition, and an insatiable hunger for knowledge. However, these unique traits come with distinct internal conflicts that can make even the idea of a career change feel paralyzing.
1. The Burden of Idea Overload
Creative individuals and entrepreneurs are prone to overflow with ideas, projects, and passions. My clients commonly report having far too many ideas in a day, which can make things feel messy and shift their focus constantly - especially when contemplating a career change or branching into new fields.
This vast array of options leads to the paralyzing paradox of choice. When faced with a million-dollar business idea or a dream of a career change that involves yoga on the beach, the inability to choose can be overwhelming and make many creatives feel stuck. This is exacerbated by the fact that many creative generalists feel misunderstood, believing that their multi-passionate brain must fit into a "tiny box of specialization". I know, believe me, this used to be me.
2. The Overthinking Cycle
The root of feeling stuck often lies in trying to solve complex life and career change questions solely using your mind.
After doing this work for a decade, I know that my coaching clients frequently desire guidance because they are at a tricky point in their career and life, or feel like they have outgrown their current life. They believe that thinking harder will produce a solution, but this only results in overthinking and worrying about the right decision, which only makes them more anxious and stressed out.
As time passes, an initial burst of inspiration can lead to a vision that grows more elaborate and turns into a mountain. This makes the task of actually doing things increasingly daunting. The result? Endlessly overanalyzing every decision you could make, especially about career change, inevitably leading to frustration or burnout before you even start.
3. The Paralysis of the Inner Critic
The final block is often the internal mechanism designed to keep us "safe," our beloved inner critic. This voice instills self-doubt and constantly says that what we want "isn’t real" or that "we're not good enough".
This constant internal chatter contributes to procrastination and self-sabotage. When clients come to me, they often have repeatedly broken promises to themselves (a side effect of procrastination), and start to question if they're even capable of achieving their dreams, especially when it comes to a major career change. Furthermore, many creatives unconsciously talk themselves out of projects by looking for flaws in every idea. This flaw-finding is often fear (False Evidence Appearing Real), attempting to stop them from stepping out of their comfort zone.
The Career Coaching Solution: Moving from Thought to Action
The fundamental shift provided by career coaching, especially during a career change, is the understanding that you cannot think yourself into a new career or life; eventually, you must go out and do it. Clients come to me for coaching precisely because they want a strategic roadmap that guides them toward a fulfilling career and helps them gain clarity and confidence to make choices aligned with their desired career change.
1. Embracing Action to Achieve Clarity
The core truth for the creative generalist suffering from idea overload is simple: ambiguity never disappears by simply thinking through all your options. When faced with multitudinous possibilities, the only way forward is to break the overthinking cycle, especially around career change, by taking action.
Clarity Through Choosing: Clarity is not a prerequisite; it only appears when you pick something. Once you choose, even if it feels scary, you start experimenting with reality, which is how you learn whether you like an idea or not, or if a particular career change actually fits you.
Embracing the First Step: My clients often face the hurdle of not knowing where or how to get started. Coaching helps them define the one thing they will get started with right now. Not forever, just for right now. This could be a small, concrete step toward a career change. This action doesn’t need to be perfect or permanent; if you don’t like it, you get to change your mind.
2. The Power of Mindset and Rewiring the Brain
Coaching is an integrative process that addresses both external plans and internal belief systems. The first phase of my four-step MOVE method focuses on Mindset.
Mindset Dictates Behavior: Your mindset influences your behavior; it is the driving force behind what you do. Overcoming mental blocks is especially critical during a career change, and it requires understanding that you are not your thoughts. You have control over what you allow yourself to believe and act on.
Neuroplasticity and Change: To achieve different results, you must change your mind, literally. Coaching uses techniques to help clients disrupt the mental, physical, and emotional systems that keep them stuck when contemplating taking action. By uncovering unconscious stuff that is keeping us stuck, we can begin healing and move forward.
3. Cultivating Self-Leadership and Consistency
Getting unstuck, whether in your current job or during a career change, is an act of personal leadership. Leadership is never given; you have to take it for yourself. This means admitting you have a role in staying stuck and realizing nobody’s coming to pull you out.
Building Resilience: You must stop waiting to feel entirely ready or confident before starting, as this is precisely what led to stagnation. The solution is not heroic bursts of energy but little changes over time that can, even quietly, spark a deeply meaningful career change.
The Chain of Action: Consistency is key. I love the Seinfeld Strategy, it emphasizes setting a goal and marking off every day you work on it; the only rule is "not breaking the chain". Small steps repeated over time (the compound effect) will move you toward your desired career change and cultivate the resolve and grit necessary to separate dreamers from doers.
By moving into this action-taker mode, you can move from being trapped in your own thoughts to feeling unstuck, moving towards your goals, and gaining the self-assurance that you are finally on the right path - whether that’s a new creative project, a passion pursuit, or a career change that fits who you truly are.
You’ve got this!
Take the First Step Toward Clarity and Freedom
Are you ready to break free from the overwhelm and finally gain the clarity you’ve been searching for? Imagine having a personalized roadmap that embraces all your passions and guides you toward a career and lifestyle that feel authentic and fulfilling.
Discover your unique path with a one-on-one private session designed to help you uncover your “glue,” silence the inner critic, and transform your scattered ideas into a focused, actionable plan.
Frequently Asked Questions About Career Change for Creatives
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If you’re feeling unfulfilled, stuck, or burnt out in your current role, it may be a sign that it’s time for a change. Listen to your inner voice - especially if you continually daydream about pursuing creative passions or feel a deep pull toward something more aligned with your interests. While there’s no perfect time, small, consistent steps can help you transition without feeling overwhelmed.
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Fear is natural during major transitions, but it doesn’t have to paralyze you. Reframe failure as a learning opportunity and take comfort in the fact that your creative nature equips you with adaptability. Start with low-stakes experiments, such as freelancing or building a portfolio, so you can explore your new path before fully committing.
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The key is to find what I call your ‘glue’ that ties your passions together. Look for overlap between your interests and skills, then identify how they can serve others or solve a problem. Think about which passion feels exciting but also sustainable over the long term, and remember - you can always evolve your approach as you grow.
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Start by researching how others in your field make a living. Look for gaps in the market that align with your strengths. Experiment with offering services, selling products, or teaching what you know. Join creative communities for support and inspiration, and don’t be afraid to start small as you test the waters.
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Not everyone will understand your path, and that’s okay. Protect your energy by sharing your plans only with those who support your vision. Use critiques as fuel to refine and improve, and remember that your unique perspective as a creative is a strength - not something to be dismissed.
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Transition gradually by starting your new career as a side hustle or part-time pursuit while maintaining other income sources. Budget thoughtfully, reduce unnecessary expenses, and look into grants, crowdfunding, or part-time contracts if needed. Focus on small wins that build your confidence while helping you stay financially secure.
Monetize Your Multi-Passionate Ideas: A Creative's Guide to Financial Freedom
Are you an artist, creative generalist, or entrepreneur who feels caught between the pressure of earning a decent living and the desire for meaningful, creative work? You're talented, driven, and educated, and you have an abundance of creative ideas. Yet, that creative energy is often overshadowed by financial anxiety, procrastination, overthinking, or the sheer exhaustion of having too many ideas and striving for perfection.
The result, as I witness daily in my coaching practice, is often stagnation and frustration. You want financial independence, but worry that making significant money requires sacrificing your creative work, leading to a job that feels empty and meaningless or a career that is slowly sucking the life out of you.
Breaking Free from the Cycle of Paralysis
After a decade supporting creatives to get unstuck, I know that the fundamental challenge for creatives and entrepreneurs, especially generalists, is transforming their multifaceted nature, often characterized by idea overload and the paralyzing fear of choosing the wrong thing, into a sustainable, profitable system that works with their complex mind and not against it.
Many creatives feel stuck in a golden cage, clinging to stable jobs out of necessity or fear, even if those roles lead to burnout or leave them feeling undervalued. But there are ways to break free from this trap and create a fulfilling, successful career that aligns with one's unique talents and passions.
Strategy 1: Redefining Value by Combining, Not Choosing
Creative generalists often have multiple projects floating in their heads, ranging from starting a business to pursuing various artistic disciplines. The internal pressure to specialize is immense in a world geared toward experts. But forcing yourself to pick only one interest often leads to rapid boredom and abandonment, famously known as "The Dip".
The key to financial stability without sacrificing your creative soul is realizing that you don't have to choose; you can combine.
Instead of trying to fit into a tiny box defined by others, seek out your unique "glue," the common thread that ties all your seemingly disparate interests together and gives them meaning. This process begins by understanding that your diverse skills, from strong writing to complex problem-solving and communication, are marketable assets.
For instance, a client with multiple interests might realize their true value lies not in what they do (e.g., writing, teaching, design), but in how they combine those skills to connect ideas, inspire change, or simplify complex concepts. When you start identifying career opportunities that utilise your full, multifaceted skill set, the work instantly becomes more engaging and sustainable.
Tip: Map out your "superhero powers," your strongest points. Then, identify the overarching purpose or value (your glue) that motivates you, even if it feels small or internal. This could be building community, equitable resource distribution, or simply inspiring genuine connections.
Strategy 2: Action Over Analysis for Breakthroughs
A common pattern I see with creative clients who are stuck is trading external hustle for internal analysis: endlessly conceptualizing and overthinking ideas to the point of "analysis paralysis". This is often driven by perfectionism, in which the inner critic demands unattainable ideals before allowing any visible action.
You cannot think yourself out of being stuck; you must take action. To break free from this cycle and find genuine momentum, focus on Execution (the E in the MOVE Method that I've developed).
Small, Consistent Steps: Instead of relying on a burst of willpower (which is a finite resource) to tackle the "huge" project, commit to consistency. I love the principle of the Compound Effect: small steps repeated over time lead to incredible, exponential results.
Tip: Implement the "Don't Break the Chain" philosophy (aka The Seinfeld Strategy). Choose one micro-action related to your new combined passion (e.g., writing for 45 minutes, outlining a business structure, or reaching out to one potential collaborator) and once you've done it, mark it with a big, bold X on your calendar for the day. The only thing you have to do is not break the chain.
Extra tip: If you're struggling with follow-through, external accountability (such as a coach or a peer) can be highly motivating too!
Strategy 3: Designing Systems for Flow, Not to Grind More
Financial stability for a creative entrepreneur with many passions and ideas means designing a work-life structure that supports your need for flow and creative rest while maximizing income potential. Many clients struggle because their work requires constant energy and presence (as a manager, designer, or event producer), leaving them exhausted and with little bandwidth for what they're actually passionate about or even the more mundane marketing, admin, or generating passive income.
To achieve financial abundance without burnout:
1. Prioritize Passive Income Streams: Actively look for ways to monetize your knowledge or creative output that detaches your income from your direct time and energy output. For creative generalists, this might involve creating an online course or digital product that simplifies a complex process or teaches people something you excel at.
2. Integrate Technical Skills Strategically: Use your intellectual curiosity and learning strengths to incorporate technical skills (like analytics, AI, or system design) not as a main job, but as tools to make your business or work more efficient. This allows you to delegate wisely and maintain focus on your creative domain.
3. Cultivate Flow and Rest: Since you thrive on creation and easily experience flow when engaged in meaningful work, structure your time to enter this state daily. I do this with a morning writing routine and daily creative habits. Be mindful that overwork and distraction can drain this energy.
Achieving financial freedom as a creative requires action. If you're waiting for confidence or clarity before doing anything, remember that being ready is a decision, not a feeling. Confidence is built through doing the thing you fear, not waiting for the fear to disappear.
Ready to build your financial foundation?
If you're tired of the constant stress, analysis paralysis, and the nagging feeling that you're not living up to your full potential, it’s time to move forward. You're an ambitious, resourceful creative leader who deserves a life that is both joyful and financially secure.
Gaining clarity and a strategic roadmap is the first step to conquering financial anxiety and multiplying your creative pursuits.
Redefining Success: Breaking Free from Expectations to Find Your True Career Path
Picture this: you’re climbing your first career ladder, but as you're getting higher, you realise it’s propped against the wrong wall. For many young professionals, this eerie metaphor becomes reality. I know, because many of them end up sitting across from me in my career coaching practice. Trapped by societal norms and familial expectations, they often find themselves chasing inherited dreams instead of their own. The weight of these expectations, often combined with the financial safety net that their well-meaning parents provide, can feel suffocating, leading to self-doubt, boreout, confusion, and ultimately, burnout.
But what if there’s a way to step off the path carved for you and start carving your own? What if the freedom you’re yearning for isn’t as far away as it feels? In this post, I will share what I've learned supporting young professionals to find the career they love: their internal struggles, but also the actionable steps that helped them shift from feeling stuck to rediscovering their purpose.
It all starts with one question: What do you truly want?
The Struggles of Living Someone Else’s Dream
The Invisible Chains of Expectations
For many of us, family plays such an important role in shaping our dreams and ambitions. Parents dream of stability for us - the prestigious job, the paycheck with benefits, the degree you’ll hang on your office wall. While these aspirations come from a good place, they can overshadow your authentic desires. Over time, the life you’re building can feel more like a tribute to someone else’s dreams rather than a reflection of your own.
Have you ever asked yourself, "Whose success am I really striving for?" It’s a hard question, especially when external pressures reinforce the idea that there’s a "correct" path to success. Knowing whether you’re living authentically or on autopilot can be a challenge.
Losing Sight of Your Personal Vision
Here’s the paradox young professionals face today. On one hand, there’s the endless array of career options made possible by technology and a globalized economy. On the other hand, that incomprehensible amount of choices can lead to analysis paralysis. Because of this, I see many young professionals struggle with questions like: “Am I making the right choice?" or worse, "What if I’ve already made the wrong one?”
This fear of committing to the wrong career path often keeps people stuck. They stop moving forward, confused and uncertain about what their true vision for themselves actually looks like. If this is you, you're not to blame. The pressure of expectations and societal norms can feel overwhelming. But here’s the truth: there’s no single “right” path, and there’s immense power in simply taking the next step - no matter how small it may be - that feels right for you.
The Looming Threat of Burnout
When you continuously chase external validation - whether through promotions, LinkedIn likes, or climbing the corporate title ranks - burnout becomes almost inevitable. Burnout is a dreamkiller because it doesn’t just leave you exhausted; it leaves you questioning your worth, your purpose, and the very goals you once thought were right for you.
The good news? You’re not as stuck as you think. Below are practical ways to break the cycle.
3 Powerful Steps to Reclaim Your True Career Path
1. Reflect on Your Values and Passions
The first step to building a life you love is understanding what truly matters to you. It’s about going beyond what society or family expects and asking yourself:
What lights me up?
What do I value most - creativity, independence, or impact?
If I weren't afraid of what my parents or friends would think, what would I do differently today?
Find some quiet time to journal or think about these questions. Reflection is like decluttering - once you sort through the mess of other people's expectations about your life, you’ll begin to see your own dreams emerge.
What you can do right now
Block off an hour each week to write down the moments that brought you happiness and fulfillment. Look for patterns over time - they might reveal hidden passions or values you’ve overlooked.
2. Experiment With New Experiences
Finding your path isn’t about having all the answers upfront. It’s about trying new things and staying open to those "Aha!" moments. Maybe it’s volunteering for causes you care about, freelancing in a different field, or even pursuing a side project. Exploration is how you discover what energizes you.
Think of it like prototyping your career or microdosing your dreams. Not every attempt will succeed, but each one will bring new insights.
What you can do right now
Pick one thing you’ve always been curious about - learning graphic design, public speaking, investing - and dedicate 30 minutes a day to it for a month. You may uncover a passion or skill you never knew you were capable of.
3. Seek Guidance From a Mentor or Professional
Sometimes, the best way to make sense of our choices is by having someone help us see things through a fresh lens. A mentor or career coach can not only guide you through uncertainties but also provide the tools and strategies to identify your strengths and goals.
The key here is finding someone who listens without judgment and encourages you to think big. A career coach’s role isn’t to prescribe a solution but to help you chart the path that feels true to yourself.
What you can do right now
Reach out to someone you admire - a teacher, former manager, or industry leader. Ask for a coffee chat and approach it as a learning opportunity. Their perspective might spark clarity on your next steps.
Breaking Free Starts With One Choice
The pain of being stuck isn’t permanent. It’s a signal that something needs to change - and that change can start today. By reflecting on your values, exploring different paths, and seeking meaningful guidance, you’re not just rejecting the mold; you’re reclaiming your agency.
Remember: You don’t have to do it alone. Imagine having someone who truly listens, who gives you the tools to rewrite your story and step into a life that feels undeniably yours.
That life, the one filled with purpose, joy, and authenticity, is within your reach. It’s not a distant dream or something reserved for others; it’s waiting for you to claim it. Every step you take, no matter how small, brings you closer to the life you’re meant to live. And through it all, I want you to know this: I believe in you.
You are capable, resilient, and worthy of every beautiful moment ahead. The power to create your path is already in your hands. Keep going – you’ve got this!
Feeling stuck or weighed down by expectations?
You’re not alone - so many talented, creative souls end up living someone else’s story, unsure how to start writing their own. It’s easy to lose clarity amidst the noise and pressure.
Let’s discover what truly motivates and inspires you. I’m offering a free session to help you untangle expectations, reconnect with your authentic values, and set your sights on a future you choose - one that lights you up.
Job Envy: The Creative Generalist's Struggle and How to Turn It into Your Biggest Advantage
As a multi-passionate, creative individual, have you ever found yourself scrolling through LinkedIn, pausing on a "perfect" job title for a specialist, and feeling a pang (or two or three) of envy? You see someone thriving in a singular, focused role – perhaps a "Senior AI Developer" or an award-winning "Cupcake Master" – and for a fleeting moment, you think, "That's it! That's what I should be doing!" This phenomenon, known as "job envy," is, unfortunately, a common experience for creative generalists.
We live in a world that largely expects us to choose one thing and become experts in it. Growing up, I realised early that this wasn't going to work for me. Creative generalists, also known as multi-passionate creatives, polymaths, or multipotentialites, are wired differently; we need to combine various interests and quickly become bored once we've figured something out. Sound familiar?
This can lead to a "patchwork of jobs" or a history of starting new projects only to abandon them when the initial excitement fades. When you see someone seemingly "sticking with it" and achieving conventional success, it's natural for that inner critic to show up, reminding you of your own perceived lack of focus or commitment.
However, this envy is often a fleeting emotion because deep down, you know that a single, narrow path wouldn't truly fulfill you in the long run. What you're truly envying isn't the entire job, but rather specific aspects of it – the knowledge, the skills, the experience, or even just the sense of clear direction that specialist seems to possess. You’re not alone in feeling like a "mish-mash of random half-baked talents" despite having expensive degrees or diverse experiences. Many creative generalists I support feel misunderstood, out of place, and never good enough when compared to society's standards of success.
The good news is, you can transform this job envy from a source of self-doubt into a powerful catalyst for your own growth and clarity. Here are three strategies that have worked for me and many of my clients to use job envy to your advantage:
1. Deconstruct the envy: figure out what you really like about this job
Instead of wanting the entire job, break down what specifically attracts you to it. What is it about that "Senior AI Developer" role that sparks your interest? Why would you like to be celebrated at a Cupcake Master? Is it the challenge of solving complex technical problems, the intellectual stimulation of working with cutting-edge technology, or the delight of seeing people truly enjoy your delirious creations? For a creative generalist, the desire is often for the knowledge or skill associated with that role, as well as the recognition of it by others, rather than a long-term commitment to a singular career path (as that, in fact, is our kryptonite).
Action: When you feel a pang of job envy, pause and ask yourself:
What specific skills or knowledge does this person have that I'd love to acquire?
What problems do they solve, or what impact do they make, that resonates with me?
What aspects of their daily work excite me, even if the overall job doesn't?
By doing this, you're not trying to become that person; you're extracting valuable "ingredients" for your own unique "portfolio career". You're combining instead of choosing, my favorite thing to do when I'm helping a client create their dream career.
For example, a multi-passionate creative might be fascinated by how an AI developer builds chatbots and workflow automation and realize they want to learn those specific skills to differentiate themselves and teach others (like I currently am), not necessarily become a full-time developer. This clarifies your focus, helping you combine different interests into a meaningful whole (as I share in my book, you're the glue binding them all together, after all), that aligns with your innate curiosity and desire (or, should I say, need) for learning.
2. Disrupt your limiting beliefs and inherited dreams
Job envy often triggers deeply ingrained limiting beliefs and "inherited dreams," as I like to call dreams that we were given through our upbringing and experiences, about what success should look like. You might be subconsciously trying to fit into a blueprint of success that isn't yours, leading to feelings of not fitting in and frustration. Your inner critic might tell you, "This has been done before, it's not original," or "You're not confident enough to be an entrepreneur". These thoughts stem from a "fixed mindset" that resists change and follows conventional paths.
Action: Use job envy as a "disruptive strategy" to challenge these mental blocks:
When your inner critic shows up, question it. Where do these beliefs come from? Are they truly yours, or are they messages you've internalized from childhood, society, or past experiences?
Apply the "Solomon Effect": view your situation from an outside perspective. Ask yourself, "What would I tell my best friend or my child if they shared the same envy or self-doubt?"
Accept that there’s nothing "wrong" with you; you might have simply been "misdiagnosed" by a world that doesn't fully understand your multi-passionate brain. This shift in mindset can help you see new opportunities in all these jobs you'd like to have (without actually leaving your current job for them) and help you to finally feel like you belong (which you do!).
3. Cultivate grit and consistent action towards your vision
The comparison trap, especially professionally, can lead to inaction, leaving you "stuck" in an overthinking loop where you analyze every option but - drumrolls please, do absolutely nothing. You might find yourself "trying everything" but "not sticking to anything". Overcoming job envy requires transforming that envy into something constructive: concrete action, even if it feels uncomfortable.
Action: Move from contemplation to execution:
Question the "One Thing" Myth: Society often pushes us to choose one thing. But as a creative generalist, you don't have to. Allow yourself to have multiple job interests and weave them together.
Celebrate your unconventional path: Your career or work history might resemble a game of Snakes and Ladders, with twists and turns. This reflects the uniqueness of your brain and passions, not a flaw to be ashamed of! Don't compare yourself to the linear paths of specialists.
Recognize the growing value of generalists in the workplace: Luckily, things are improving, and more and more companies are hiring for skills and talents, actively looking for generalists who can juggle many hats and create bridges between ideas, projects, and people.
Remember, your diverse experiences and wide-ranging interests are your SUPERPOWER. They allow you to see possibilities and connections that others often overlook. The path you have walked, with all its twists and turns, is what makes you uniquely capable of tackling challenges with creativity, innovation, and resilience.
Own your story, lean into your strengths, and trust that your vast t-shaped breadth of knowledge and adaptability are exactly what the world needs. You are not an exception - you are an asset. Always believe in the power of being unapologetically, authentically you. I know I do!
Ready to Turn Your Multi-Passionate Job Envy into an Advantage?
Feeling stuck and unsure of how to channel your many passions into a fulfilling career can be overwhelming but here's the truth – your multi-passionate nature is a gift, not a burden.
If you're tired of just thinking about your goals and want to start working on them, let's connect for a free one-on-one coaching session. Together, we can find your own answers, chunk up your big projects, and help you find the flow and confidence to build the life and career you truly want.
Building Your Creative Income: 7 Practical Steps for Financial Freedom with a Portfolio Career.
Even though the days of job security and one job for life are long gone, the idea of it being replaced by a career solely focused on one area of expertise is also becoming outdated. Especially with the rise of the gig economy, more and more people are turning to portfolio careers to build their creative income. A portfolio career means having multiple sources of income, often in different industries or areas of work, rather than relying on one full-time job.
For many creatives, especially generalists, this type of career may already be familiar - working on freelance projects while having a part-time job or taking on various side gigs. But with careful planning and deliberate action, a portfolio career can be a sustainable and fulfilling way to build your creative income and achieve financial freedom while doing work you love!
In this article, I share insights from working with creatives (for a decade now!) on how to create a portfolio career that works for you. I hope it will inspire you to follow your career dreams and embrace the opportunities that come from having a portfolio career.
Embrace your unique generalist nature
As a creative generalist or someone with many interests and passions, the traditional linear career path with a single job and source of income often leads to bore-out, especially if your talents are being underutilized (which they usually are). Instead, a portfolio career combines multiple income streams aligned with your passions, interests, talents, and skills. That's the amazing part! But, however exciting this approach can be, it often feels financially precarious.
Many of my clients have expressed concerns about financial stability while pursuing their creative endeavors, a recurring theme when onboarding new coaching clients. They might feel like they don't have their "shit together." Or they might have innovative business ideas they're unsure how to market, like this wonderful creative who has been in wine and restaurant management before having a child and who came to me while working on a nut-free energy bar recipe geared towards new mothers, also considering an app focused on mother care. A typical way for a creative generalist to connect seemingly unconnected dots or, as I like to say it, discover their unique "glue."
7 Practical steps for financial freedom with a portfolio career
As a creative (generalist) and entrepreneur, building a multi-source income stream is crucial for long-term financial sustainability while allowing you the freedom to do work that truly fills you up. Here are some practical steps that worked for me and many of my clients to help you create your own thriving financial foundation:
#1 Map your talents and skills, and learn to appreciate them
As someone with a creative and entrepreneurial mind, you have many skills, talents, and interests. That's a given. But being clear about what you're good at and enjoy doing isn't always straightforward. Make a comprehensive list of everything you can do, from your professional experience to your hobbies and creative pursuits.
Consider how each of these can potentially generate income or how you could combine a few into a career. Don't underestimate the value of seemingly unrelated skills or interests; they can often be combined in unique and profitable ways.
#2 Diversify your income streams strategically
Multiple income streams are the cornerstone of a portfolio career and decide its financial sustainability. This can include freelance work, a part-time job (or "good enough job," as Barbara Sher calls it in her book Wishcraft), selling creative or online products, teaching workshops, consulting and coaching, or developing online courses.
The goal is to create a mix that provides both a stable base and opportunities for growth. Consider how you can use your different skills, talents, and interests to create a mix of income streams for your portfolio career.
#3 Understand that fear is the dreamkiller
As you start building a portfolio career, or if you've been thinking about what you could do for a long time but haven't taken any substantial action toward one or more ideas yet (hello, unfinished projects on the shelf, I see you!), it's important to acknowledge and understand that fear can be a major roadblock. Fear of failure, rejection, and not being good enough are all common fears that can hold us back from pursuing our dreams. The insidious thing is that fear often doesn't show up as fear. It disguises itself in very well-packaged excuses, such as "I don't have enough time" or "I'm not ready yet," or as perfectionism, people-pleasing, or procrastination.
It's important to remember that fear is just a feeling, and feelings can be managed and overcome. It's about shifting your perspective and learning to work through your fears.
#4 Price your services and products high enough
Many creatives struggle with pricing their work. Remember that your unique mix of skills and perspective brings significant value. Research industry rates, but also consider the value you bring to each project. As mentioned in my book "Get Unstuck!," building a business that feels right and using marketing practices aligned with your values is important.
Don't undervalue your expertise out of fear of not being good enough. Instead, price your services and products high enough to reflect the value you bring to the table. It is important for you to get fair compensation for your work and to help you build a sustainable business model.
#5 Collaborate and network with other creatives
Collaboration and networking are key components to any business or career, but as a creative generalist, I find it's more important than ever. We are still living in a world of specialists, and that can erode our self-worth and talk us out of our portfolio career dreams. By connecting with other creatives, you can expand your skills and knowledge through learning from others. Additionally, collaborating with others allows you to work on projects that may have been too large or complex to take on alone or that you were too scared to even start with!
My exclusive community, "Gen Spark," is here to do just that: facilitate collaboration and connection among creative generalists. Click here to discover more and become a member.
#6 Manage your finances mindfully
Financial management is key to making your portfolio career work - or any career or business for that matter. After working with creative entrepreneurs and generalists for a decade, I know that the admin and financial side of their careers and business are often not their strong suit. However, this doesn't have to stop you from being successful. With mindful and intentional financial management, you can stay on top of your finances and make good decisions about your career and business.
To start, it's important to understand the basics of personal finance, such as budgeting, saving, investing, and managing debt. This will give you a solid foundation for making financial decisions that align with your goals and values. I know it sounds scary, but you can do it!
#7 Never stop learning and growing
Continuously learning and developing your skills is important for a successful portfolio career. But one thing that is more important than any other is learning how your creative brain works. That is why psychoeducation into the uniqueness of your creative brain is part of my work with my clients.
How good is it to know how you should do something if you are unaware of how your brain actually operates? Understanding your strengths and weaknesses and how to work with them can be a game changer in your portfolio career.
Building your creative income as a creative generalist takes time, intention, strategic planning, and an unwavering belief in the value and uniqueness of your multifaceted self. But once you have laid the foundation and established a solid portfolio career, the possibilities are endless.
Ready to take real steps towards building your own thriving portfolio career?
Are you done with being confined to just one career path and ready to embrace your multi-passionate nature? Are you tired of feeling like you have to choose between your different passions and skills?
I can help! In fact, liberating creative generalists from the 9 to 5 is what I do best. Let's discuss your unique skills, passions, and financial goals and start mapping out a strategy for your portfolio career.
How to Create a Portfolio Career as a Creative Generalist
Throughout my life, I never set out to stay doing the same thing for too long. It’s always been my dream to live in NYC, for instance, and while it might not happen for a while, it makes me think about how I organize my life and career into buckets and how unusual that is for entrepreneurs. Most people I meet think they have to stick to one career for their entire lives, but really, we have the power to change and evolve whenever we want.
In my coaching business, I hear all the time how my clients are being pulled in all these different directions and they don’t understand how to rationalize their innate need to do different things, take on different roles, with society’s need to settle them into a specific box. For instance, doctors aren’t supposed to be coffee shop owners who sit on the board for toy companies. And entrepreneurs who own companies that distribute luxury amenities aren’t also supposed to have kitchen cabinets importing businesses…right?
Well, why not? Why can’t we do everything we dream of doing and every opportunity that comes our way that lights a spark inside of us?
Here’s the truth: we can. And I help clients do it every day.
Take my own story for instance, my career portfolio includes business and career coaching, writing books, speaking engagements, investing in small businesses, and creating new businesses - like my conference in the fall and my soon-to-be-launched Creative Generalist Network (more to come on that below!). And before that, even though I went to university to pursue a masters’ degree in philosophy and ended up working for, and founding, several web agencies.
The path we are on right now doesn’t have to be the path we stay on forever. There is no shame in jumping around - in fact, it’s empowering. This need for variety is what makes us creative generalists. We were never meant to fit into the classic 9-to-5 life, and when we fully embrace our creative generalism, we have a leg up when it comes to pursuing our dream career paths!
So how do we pursue a portfolio career that bolsters our ability to excel as creative generalists?
Various income streams. Have various income streams so that as you flow between the different roles, you never have to sacrifice your wants for your needs. You might try adding to your earned income with investments, online courses that require upfront effort to create but quickly produce passive income, and freelance consulting. However you choose to gain income, there’s power in having multiple streams at your disposal.
Don’t choose, combine. Stop trying to choose a particular career or project, learn to combine them. The beauty of a portfolio career is that there are no rules. You can do anything you want! (This is one of my superpowers. Let’s talk if you want help with this!)
Talent stack. Figure out your talents and skills and start stacking them to create a sweet spot that will raise your value in whatever field you’re interested in. For instance, if you are a copywriter who is also an audio engineer, pitch your talent to a podcast production company looking for a marketing guru who can also clean and treat the sound on the rough recordings.
Learn new skills. Are you a web designer who’s always been interested in teaching ballet classes to preschoolers? Or a college student studying molecular biology who also wants to write fiction novels about underwater gateways to other planets? Whatever it is that you think you might enjoy, go after it. Never stop learning. Go where your inspiration takes you!
Stay open-minded. You never know what you might learn from other people’s perspectives. Staying open-minded allows you to connect easily with others, building networks, and furthering your work and life in ways you might not expect.
Find a work-life balance. While individuals in mono-type roles don’t have to worry about their work invading their personal lives, creative generalists do. Our work is so varied and flexible, that sometimes that flexibility works against us, allowing business to bleed into our personal lives. The best way to combat this is to create a work-life balance that is sustainable to maintain.
Embrace change. Instead of trying to fit into a particular role, embrace jumping from role to role. The beauty of a portfolio career is that you don’t have to stick with the traditional career path, which includes sticking it out in a business or job you hate. Feel free to shake things up!
Find your community. Creative generalists tend to be isolated because of the solitary nature of their careers and work versatility, but finding your community is the best way to help you succeed. As a creative generalist myself, I created the TrueSpark community to help my clients and readers engage with like-minded individuals who will help them find inspiration and opportunities to grow.
Understand your why. Many people fall into a portfolio career, while others plan extensively for them. Either way, you should know why you are pursuing it now. Do you want more flexibility? Do you want to pursue every idea you’ve ever had? By knowing your why, you will be able to identify your creative generalist values more easily, which will in turn help you create the life you’ve always dreamed of!
Keep at it. Don’t give up when things get tough or confusing. Keep going and know that it will happen. The roles will come. The income will flow. And the fulfillment and success will bloom.
Building a portfolio career - like we generalists like to call it - is a lot easier than you think. There’s no need to toil away at work you don’t enjoy, or to sift through ideas and goals until you find the one most acceptable by the internet. You can have multiple passions or interests, pursue them all, and be better for it. It’s a lot more beneficial to your soul! When our work is aligned with our hopes, dreams, wants and needs, we can achieve anything.
Take small steps everyday and before you know it, the life you want will be right in front of you.
Scared to embrace your portfolio career?
Stepping outside the “norm” can feel overwhelming for anyone, especially if you’re a creative generalist with a streak of perfectionism. But pursuing your portfolio career is less about nonconformity and more about embracing who you are inside.
You were never meant to sit in a job or career you don’t enjoy. It’s time to follow that little voice inside you that tells you it wants more, it needs more…it deserves more. So stop limiting yourself. In our coaching sessions, I not only help you take that first step towards the life you actually want, but I help you build a roadmap to the exact spot you want to land!