From Climbing the Corporate Ladder to Feeling Free as a Solopreneur
by Maggie Blackburn
A year ago, I left my corporate job after a decade in tech product marketing and consulting. There was a steady realization that the path I was on no longer felt like mine but rather than listen to the voice that told me I needed to change, I ignored it until it all came to a head three months into a new job my gut told me not to take.
The decision to leave didn’t happen overnight and the transition wasn’t simple, but what I discovered on the other side has been the most rewarding risk of my life: creating a portfolio career built on multiple interests that doesn’t have to look like anyone else’s.
It looks like planning retreats and community events, coaching, hosting on Airbnb, and writing my Feel Free newsletter. It doesn’t fit into one neat job title and that’s exactly the point.
Looking back, three practices made this shift possible: listening to myself, experimenting before I felt fully ready, and building a bridge that gave me confidence to keep going.
How I Knew It Was Time to Leave
For a long time, I tried to convince myself to push through and constantly asked myself, “Why couldn’t I be like everyone else?” The colleagues I had who worked a corporate job, climbed the ladder, and were happy with their 6-figure salary. I wanted to take the easy route but, deep down, I knew I needed to finally make a change.
After my fourth new boss and a rejection to be transferred internally to the events team, I took a leave of absence to reflect. Away from the noise of work, I realized that while there were so many unknowns in leaving, I couldn’t stay.
There’s never a “perfect time” to quit, but there can come a time when the belief in yourself becomes stronger than the pull to stay (if you work on that belief in yourself of course!).
How I Experimented My Way Forward
When I first started exploring new directions, I thought I needed the “perfect” next step before I could act. I had dozens of informational chats and tried to think my way into clarity, but it didn’t work.
What finally helped was reframing my career as an experiment. I ran small tests, like teaching Pilates and helping small businesses with social media. Some things clicked, others didn’t, but each one gave me data about what energized me and what didn’t.
The more I followed my curiosity and experimented, the more I realized clarity comes from doing, not overthinking.
How I Built My Financial Bridge
Leaving without a plan felt scary. I needed to figure out how I would sustain myself while figuring out my next step. So I built my financial bridge: a way to get me to cross from a 6-figure corporate job to self-employment with confidence.
Building my financial bridge had three parts:
Rewriting my money beliefs: Letting go of guilt and scarcity, and creating new beliefs around money that supported my future.
Getting clear on my numbers: Tracking where I was spending against my living expenses and making small adjustments where needed.
Creating a plan: Defining how much bridge income and savings I needed before stepping out securely.
The bridge wasn’t permanent. It’s meant to be temporary scaffolding to support your stability while building so you can get safely to the other side.
Just Start
One of the biggest lessons I’ve learned is that you don’t need to have the whole path mapped out to begin. You just need to start. Start with one step, one experiment, one decision to trust yourself.
That’s why I’m launching Just Start, a group program designed to help multi-passionate people who want to pivot their careers but don’t want to walk away from the financial stability they’ve worked so hard to build. Together, we’ll implement your unique career experiment and build your 1-year roadmap to make it happen with structure and support. The hardest part isn’t always knowing exactly what to do, it’s just starting and figuring it out as you go.
An Invitation Forward
My journey out of corporate life hasn’t been linear or easy, but it has been deeply fulfilling because I don’t regret taking a bet on myself. Each step has brought me closer to work and a life that feels uniquely mine and most importantly, free.
If you’re considering a career pivot, know this: you don’t have to leap blindly. You can prepare, experiment, and build your bridge. Along the way, you might discover that you’re already ready but just need to finally take the leap.
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About Onward
Onward is a membership for healthcare, perks, and career support to help you thrive, no matter how your work is classified. Whether you’re self-employed, between gigs, or exploring alternatives, Onward gives you access to benefits that fit your life on your terms.
Learn more at onwardbenefits.com.
