Leaving Corporate to Reinvent Your Life
What happens when the career and life you carefully planned no longer feel like the life you want? For many women considering a career change, the hardest part isn’t knowing they’re unhappy. It’s figuring out what comes next.
Do you find another job? Leave corporate altogether? Start a business? Take some time to figure things out? And after spending 10, 20, or even 30 years building a career, is it really possible to reinvent yourself without starting from scratch?
On the Second Act Success Podcast, I sat down with author, coach, and former corporate strategist Becca Eve Young to talk about career reinvention, entrepreneurship, starting over, and what can happen when life forces you to rethink everything.
Listen to episode #270 of the Second Act Success Podcast about this topic below…
Listen on Apple | Spotify | Amazon | YouTube
Becca’s story is not a neat, perfectly planned career transition. It’s messy. And that’s exactly what makes it so relatable.
Her career began in interior design before the housing collapse disrupted that path. She went back to school for her MBA and transitioned into marketing and branding, eventually working in roles connected to major companies and brands, including Calvin Klein.
Then came another unexpected turn. In 2019, Becca traveled to Mexico for a six-month work assignment. She was supposed to return to Portland in April 2020. Instead, the pandemic hit, the travel industry collapsed, and Becca lost her job while navigating a divorce, the illness of her father, the loss of a friend, and isolation in Mexico.
Suddenly, the question wasn’t simply, “What’s my next job?” The question became, “What do I actually want my life to look like?”
Career Reinvention Often Begins When Something Stops Working
We tend to imagine career changes as carefully orchestrated decisions.
You decide you want something different. You make a plan. You find the perfect new opportunity. You give notice. Then you happily walk into your second act.
Real life doesn’t always work that way. Sometimes career reinvention begins with burnout. Sometimes it’s a layoff. Sometimes your priorities change. And sometimes several parts of your life change at the same time.
For Becca, this wasn’t her first experience with career uncertainty. Her interior design career had been impacted by the housing collapse, and she had previously experienced another corporate layoff after an acquisition. By the time she lost her job during the pandemic, she began questioning whether she wanted to continue being dependent on large corporations for her livelihood.
If you’re going through a career transition right now, you may recognize that feeling. The job that once felt secure doesn’t anymore. The career you spent years building doesn’t excite you. Or the definition of success you followed for years suddenly doesn’t fit.
That doesn’t necessarily mean you made the wrong choices. It might simply mean you’re ready for different ones.
When Life Gets Messy: Leaving Corporate, Starting a Business & Finding Your Second Act
Career Burnout Can Be a Signal to Slow Down
One of the most interesting parts of my conversation with Becca was what happened when her incredibly busy life suddenly stopped.
She had been accustomed to long workdays, meetings, deadlines, and constant movement. Being isolated in Mexico forced her to slow down.
She began hiking, cooking, meditating, journaling, spending time outside, and asking herself questions she hadn’t had time to consider before.
Eventually, one question became impossible to ignore: What am I doing with this one precious life?
Becca didn’t immediately know what her new career would look like. But she did realize two important things: she wanted to work for herself, and she wanted her work to be something she cared deeply about.
That’s an important distinction for anyone experiencing career burnout. You don’t necessarily need to know exactly what you’re doing next before you acknowledge that something needs to change.
Sometimes the first step in a career transition is simply giving yourself enough space to hear what you actually want.
Leaving Corporate Doesn’t Mean You Need to Have Everything Figured Out
After returning to Portland, Becca made a dramatic decision. She sold her belongings and returned to Mexico, where she began creating a completely different kind of life. She moved farther south to San José del Cabo and began reconnecting with things she’d once wanted, including living near the ocean, slowing down, and learning to surf.
But there was still one pretty important question: How was she going to make money?
This is where Becca’s story offers an especially useful lesson for anyone thinking about leaving corporate to start a business. She didn’t immediately invent a completely new career. She started with what she already knew.
Your Corporate Skills Can Become the Bridge to Entrepreneurship
Becca had years of marketing and branding experience. Rather than throwing that expertise away because she wanted a new life, she used it to begin working with clients as a fractional CMO.
She reached out to people she’d met through her previous work and essentially asked, “Do you need help with marketing?” That allowed her to generate income while working for herself and gave her breathing room to explore what she wanted her larger second act to become.
This is something I talk about often with women who want to leave corporate and start a business. Your first business doesn’t have to be wildly different from everything you’ve done before. In fact, one of the fastest paths to entrepreneurship can be asking:
What do people already pay me to know how to do?
Could I offer that skill independently?
Could consulting, freelancing, or fractional work create income while I build something else?
What experience have I accumulated that another person or business would happily pay for?
Your existing skills can become the bridge between employee and entrepreneur. You don’t have to burn everything down to create something new.
Starting a Business Includes Experimenting With What Doesn’t Work
Becca didn’t immediately land on the perfect business model. She experimented.
At one point, she explored selling handmade products online through e-commerce. But she discovered that the products didn’t translate well online. Customers needed to see and experience their craftsmanship in person.
When she brought the products into a physical store, they sold quickly. The experiment taught her something. And that’s entrepreneurship.
We put tremendous pressure on ourselves to choose the “right” business idea before we begin. But starting a business is often less about knowing exactly what will work and more about being willing to test, learn, adjust, and try again.
A business idea that doesn’t work isn’t necessarily wasted time. It gives you information. That information helps you make a better next decision.
How Do You Know What Business to Start?
Eventually, Becca began looking back over her career and noticing patterns. She realized she loved creating things, solving problems, developing new processes, and figuring out what came next. She also realized how much she loved helping other people escape corporate life and create something of their own. That realization led her toward coaching.
Her years of corporate marketing and branding experience hadn’t disappeared. Neither had her consulting experience. Instead, all of those pieces began coming together into something new.
This is one of my favorite exercises when you’re trying to discover your second act career or decide what business to start. Instead of asking only: “What am I passionate about?”
Look backward.
What have you consistently been good at?
What kinds of problems do people ask you to solve?
Which parts of your previous jobs energized you?
Which parts drained you?
What do you find yourself helping friends or colleagues with?
What would you happily talk about for hours?
Your next business idea may already be hiding somewhere inside your previous career.
Entrepreneurship Requires More Than Having the Right Skills
There’s another side of starting a business that doesn’t get talked about enough. You can be extremely talented and still struggle with entrepreneurship.
When Becca began working for herself, she discovered how important accountability and discipline were. Without a boss, office, or clock telling you where you need to be, you’re responsible for creating your own structure.
She eventually hired a coach herself and found the outside perspective and accountability incredibly valuable. As she put it during our conversation, “You can’t read the label from inside the jar.”
This is especially relevant when you’re transitioning from employee to entrepreneur. You’re no longer responsible only for doing the work. You’re the CEO. You’re making decisions about your offer, pricing, marketing, branding, sales, operations, finances, and strategy.
And sometimes the hardest person to give advice to is yourself.
Your Second Act May Be About More Than Your Career
Becca’s career change eventually became part of a much larger personal reinvention. Her experiences with loss, divorce, career upheaval, grief, healing, and rebuilding ultimately inspired her memoir, It’s Gonna Get Messy.
Writing the book took approximately three years and required Becca to revisit some of the most difficult periods of her life. She describes the process as deeply cathartic and credits it with helping her develop greater awareness of her own choices and experiences.
And that’s something worth remembering when we talk about second acts.
A second act isn’t always simply: “I used to be an accountant, and now I’m a business owner.”
Sometimes it’s a much bigger shift in how you want to live. It’s asking:
Who am I now?
What matters to me?
What am I willing to let go of?
What do I want more of?
What kind of work supports the life I want?
That last question is especially important. Instead of designing your entire life around your career, what if you designed a career or business that supports your life?
You Don’t Need to Hide the Messy Middle of a Career Change
Near the end of our conversation, Becca shared another important lesson from writing her memoir. She was terrified to share some of her most vulnerable experiences. But after people read the book, she repeatedly heard some version of: “Me too.”
Her advice to anyone currently going through the messy part of life is to find trusted people and spaces where you can talk about what you’re experiencing.
Because when you’re navigating a career change, divorce, burnout, entrepreneurship, loss, or another major transition, it’s incredibly easy to assume you’re the only person who doesn’t have everything figured out. You’re not.
Becca believes that sharing our difficult experiences can create connection and help other people feel less alone.
How to Start Your Own Career Reinvention
If you’re reading this because you’re considering a career change or thinking about leaving corporate to start a business, don’t put pressure on yourself to figure out your entire second act today. Start smaller.
Look at the career you’ve already built and identify the skills you could bring with you.
Think about what you want your life to look like, not just what job title you want next.
Explore ways to test a business idea before making a major leap.
Consider consulting or freelancing as a bridge into entrepreneurship.
Give yourself permission to experiment.
And most importantly, don’t mistake uncertainty for failure.
The messy middle is still movement.
You don’t need a perfect plan before beginning your second act.
You just need to start paying attention to what your life might be asking you to change.
Listen to the full conversation with Becca Eve Young on the Second Act Success Podcast for more about leaving corporate, career reinvention, entrepreneurship, writing It’s Gonna Get Messy, and building a life on your own terms.
And if you’re thinking about starting a business or growing the one you’ve already started, you can also book a free Second Act Strategy Call with me.
👉 Book your free strategy call with me at https://secondactsuccess.co/strategy
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