Rewriting Your Career Story (One Side Hustle at a Time)
I've been thinking about side hustles lately. Not the kind that business gurus might tell you to start at 4am before your day job, or the kind that hustle culture glorifies as the path to early retirement. I'm thinking about the quiet kind that begin as whispers in my sessions.
"I think I'd love to open a marketing business someday," a client once told me, her voice dropping to almost a murmur, as if saying it too loudly might jinx the possibility or, worse, invite judgment.
This wasn't a woman who lacked confidence. She was a high-achieving professional with advanced degrees and more than a decade of experience in her field. She managed complex cases, led teams, and made critical decisions daily. But when it came to voicing this other dream, this other version of herself that existed alongside the accomplished professional, her voice became small.
As the years go by, I’ve watched her and other’s journey from that whispered confession to realized businesses. Some have stayed in their roles, others haven’t. But, what’s changed was how they carried themselves through their work. Something had awakened in their career story that had been dormant for years.
I've been working with women for over six years now, navigating the complex relationship between motherhood and work. How to make complicated decisions, further their dreams, manage stress, remain inspired, work themselves out of burnout—these are the issues I see daily. You can't imagine the kinds of dreams I've gotten to see come to life that started as places of doubt, almost whispers when I first heard them in session.
One mechanism that has been particularly inspiring to witness in my clients' lives is the development of “side hustles” and what that actually does for them psychologically. It's not just about the extra income (though that matters). It's about what happens to their sense of possibility.
Why Side Hustles Matter More Than Ever
Technology has completely transformed the accessibility of entrepreneurship. Micro businesses can be built with minimal startup costs and without extensive experience or education upfront. This democratization of opportunity has opened doors that were previously closed to many, especially parents managing the complex demands of raising children while maintaining careers.
But there's something deeper happening beneath the practical benefits. The psychological hunger for autonomy and creativity may be what's really driving this phenomenon.
I see it most clearly in my clients who are high-achieving women in demanding fields—doctors, lawyers, executives, researchers. Women who have followed relatively straight-line career paths: high school achievement, competitive colleges, graduate programs and intense training, and then ascending through their professions, often while simultaneously navigating pregnancy, maternity leave, and returning to work with young children.
There's a particular kind of burnout that happens not from lack of success, but from lack of agency. From feeling that your career is happening to you rather than being created by you. From knowing you're good at what you do, but no longer remembering why you chose to do it.
And here's the paradox that initially confused me: How does adding more work actually heal burnout?
It shouldn't make sense. And yet I've witnessed it repeatedly. Women who are exhausted by their 50-hour work weeks somehow find renewed energy for their 10-hour side hustles. Why? Because the nature of the work, the relationship to the work, is fundamentally different.
How It Starts: The Whisper of a Dream
My clients rarely come to me saying, "I want to start a side hustle." They come saying things like:
"I used to love my work, but now I just feel numb."
"I'm good at what I do, but I don't know if it's what I want anymore."
"I feel like there's something else I'm supposed to be doing, but I have no idea what."
That's when we often turn to vocational assessments—not the kind you took in high school that spit out a list of possible careers based on aptitude. These are tools that help us understand what I think of as your work personality or vocational profile.
We explore questions like: What patterns emerge in the work activities that energize rather than drain you? Do you naturally gravitate toward organizational projects, or would you rather someone else handle those details? What interests captured your attention throughout your education, even if they never became part of your career path?
This assessment process isn't about finding the "right" career. It's about recovering parts of yourself that may have been set aside in the climb up a particular ladder. It's about remembering that you are more than your job title or the institution that employs you.
One thing I tell clients who feel intimidated by starting something new: "You're not starting from scratch—you're starting from depth." All those years of professional experience, of solving problems, of navigating complex systems? They translate. You bring that wealth of experience to whatever new thing you create.
But I won't lie to you—making moves after the assessment phase can be uncomfortable. It's a season of brainstorming, experimenting, and trying on ideas that feels messy to those of us who crave clarity and certainty. What problem am I solving? What unique approach am I bringing? What does the market research say? What's my pricing and marketing plan?
It's overwhelming. And while AI and other resources have made this easier than ever before, there's a risk in leaning too heavily on them too soon. I can always tell when someone has worked extensively with AI before coming to me, because their business ideas often lack soul. They prioritize market trends over personal meaning, optimization over authentic expression.
Which completely misses the point of why we're doing this in the first place.
What Side Hustles Really Do
The most fascinating part of this work is seeing the surprising outcomes that emerge. Here are the patterns I've noticed over and over again:
First, side hustles build confidence and courage that spill over into every area of life. There's something about creating something from nothing, about being wholly responsible for both the successes and failures, that develops a muscle most institutions never ask us to flex.
Second, they help women articulate and enforce boundaries in their primary work. I've watched women who struggled for years to say "no" to additional projects suddenly find their voice after launching a small side business. It's as if having another place to direct their energy and attention clarifies what matters and what doesn't.
Third, and perhaps most surprisingly, side hustles often reignite interest in existing work. I've seen clients who were on the verge of quitting their W-2 jobs discover a renewed appreciation for aspects of their work they couldn't get elsewhere—the collaboration with talented colleagues, the stability, the impact on a larger scale.
What they needed wasn't to leave their jobs. What they needed was to envision their work and career without being wholly defined by the institution, to lighten the pressure of people-pleasing within their local context, and to build something that gave them a sense of a financial future of their own making.
A side hustle can create a new professional identity that exists alongside—not in opposition to—identities tied to caregiving or institutions. It creates a space where you're not primarily someone's employee, or someone's mother, but simply yourself, creating something that matters to you.
For some of my clients, the side hustle eventually becomes their full-time work. But that's not necessarily the dream outcome. The real victory is in revitalizing someone's career story.
There's nothing more heartbreaking to me than when a career story peters out and moves to a place that feels like a tragedy. Not necessarily trauma, but a story that ends with sadness, constant frustration, or worst of all—indifference. When a career story "dies a little bit" and someone spends years just going through the motions, showing up without really being present.
I'm passionate about supporting people to keep their career stories alive, particularly mothers. And a side hustle can be a powerful tool to work out of burnout—which sounds crazy, because it's more work! But it's work with a different quality, work that you shape rather than work that shapes you.
The Danger of a Side Hustle Becoming a New Trap
I want to be clear about something important: without intention and boundaries, a side hustle can become just another path to burnout.
I've seen it happen. The excitement of creating something new can be so intoxicating that it becomes all-consuming. The business that was supposed to create more freedom becomes yet another taskmaster, with demands that expand to fill every available moment.
That's why it's crucial to think about not just what you're building, but how you're approaching that building process. What energy are you bringing? What boundaries are you setting from the beginning? What does sustainable growth look like for you specifically, given your life circumstances, values, and wellbeing needs?
This is especially important for mothers and other caregivers, who are often already operating with limited margins in their lives. Adding a side hustle without subtracting something else, or without creating clear containment strategies, can quickly lead to overwhelm.
I often work with clients to develop what I call "success metrics beyond money"—ways of evaluating whether their side hustle is truly serving them that go beyond financial returns. These might include:
Does this work energize me more than it depletes me?
Am I learning and growing in ways that feel meaningful?
Does this endeavor allow me to express values that matter deeply to me?
Is the pace sustainable given my other commitments?
Does this work enhance or diminish my relationships with people I care about?
When we're clear about these broader measures of success, we're less likely to fall into the trap of overinvestment or obsession. We can approach our side hustles with intention rather than urgency, allowing them to unfold at a pace that enhances rather than detracts from our wellbeing.
Revitalizing the Career Story
I believe career stories are living entities—capable of growth, transformation, and yes, rebirth. They don't follow linear paths, and they certainly don't have to end with the period of intensive caregiving that parenting demands.
Most of my clients didn't know what they wanted when they started this process. They just knew they wanted something more. That vague longing, that sense that there should be more to work than what they were experiencing, was actually the beginning of a new chapter in their career story.
The most powerful shift I see is when a woman reclaims her sense of authorship. When she moves from feeling that her career is happening to her to recognizing that she is creating her career, even within constraints.
A side hustle isn't just about income—it's about authorship. It's about creating a space, however small at first, where you get to write the rules, set the pace, and express your values without filtering them through an institutional lens.
I think about the client who started that marketing business. What changed wasn't just that she had an additional source of income or creative outlet. What changed was how she saw herself—as someone capable of creating something from nothing, of taking a risk and surviving it, of being a beginner again and finding joy in the learning process.
When she went back to her job on Mondays, she carried that expanded sense of self with her. She began advocating for changes she wanted to see in her department. She mentored younger colleagues with a new confidence. She set clearer boundaries around her time and energy.
Her primary work didn't change—but her relationship to it did. And that made all the difference.
What Might Be Whispering in You?
I wonder what dream might be whispering in you right now. What idea keeps returning, even though you've tried to dismiss it as impractical or selfish or just not the right time? What activity brings you a sense of flow that you rarely experience in your daily work?
There might be a small business idea germinating there. Or perhaps it's a creative practice, a research project, a community initiative, or a skill you want to develop. The form matters less than the spark—that sense of possibility and agency that has perhaps gone dormant in other areas of your work life.
What part of your career story feels stuck, stagnant, or even "dead"? And what small, experimental step might begin to revive it?
I believe deeply in the power of these small beginnings, these tentative experiments that over time can transform not just what we do, but how we see ourselves as the authors of our own careers. If there's something whispering in you, I hope you'll find the courage to listen—and perhaps to whisper back, "Yes, let's try."
If you're feeling that whisper of a dream or just a vague sense that there should be more to your work than what you're currently experiencing, I'd love to help you explore what might be next. Book a career clarity session where we can listen together for what wants to emerge in your career story. As a career coach specializing in working with high-achieving women navigating both career evolution and motherhood, I bring both professional expertise and personal understanding to this journey.
