The narrative is black and white in an experience that is gray all over.
I left my corporate job AND I miss leading a team.
I work for myself AND my days are much more peaceful.
I have my time back AND my ambition still takes up mental space.
I have independence AND more financial risk.
I was a CEO who answered to a board of directors AND now the only person I answer to is myself. This is simultaneously freeing and overwhelming.
I love the beauty of the “I left corporate and I’m living my best life” narrative. It’s a good story. It’s clean, it’s inspiring, it fits in a caption. And yet, it’s a highlight reel of a very nuanced experience. My situation is gray all over and I’m willing to bet it is for anyone else who has left as well.
Leaving With a Plan Doesn’t Equal No Emotional Pain
I’m a financial planner and a former Co-CEO of a multi-billion dollar Registered Investment Advisory firm (RIA). I wasn’t going to leave a role like that without the pieces in place first, and I didn’t. Thanks to years of work and savings, I left from a position of work optional, meaning I’m doing this work because I want to, not because I have to. A detailed timeline and plan was put in place for myself and for the company.
And yet, even with all of the planning, I still miss leading a team. And yes, I love my freedom, but my ambition didn’t die with my exit. It’s still alive and well, some days needing to be checked more than others. (Past me is always guilty of having more ambition than future me.) I’m a financial planner. I had a damn good plan in place. But all of that planning didn’t magically make the emotional vacillation disappear. It just meant I got to feel it from solid ground instead of free falling.
We should note that this isn’t the first time I left corporate.
I started my first business back in 2013 after 10 years in the financial services industry. It was during that time that I really wanted to serve a different set of clients and I really wanted to build my own path. I was at odds with the opportunity being laid out in front of me with my existing employer. And so I quit. Just kidding. I took about a year of building up resources and had in-depth conversations with my partner and then made the transition to building my own business with a foundation in place.
What Will Replace The Structure You’re Leaving?
Leaving a leadership role and most corporate roles isn’t just leaving a job. It’s leaving a structure. A CEO reporting to a board has oversight and also a room of people to think with and people to lead. People whose job it is to push back before you act and people who look to you for guidance on vision and goals to pursue next. There is a cadence of accountability that can both push you to your best and simultaneously add six months to your project.
Not having that room to lean on can be hard depending on the day. Sometimes you want to bounce ideas around on the spot. Others, you could use some support in execution. While I no longer have a board of directors I report to and a team of 70+ that I lead, I’ve found ways to rebuild a version of this on my own terms. I’m in study groups and masterminds with other business owners who will tell me when they think I’m wrong. I have a list of industry friends on speed dial that I can connect with. I’ve taken time to rebuild my list of experts I lean on for everything from compliance to design to scheduling. It’s not the same as a board and a direct team, but it’s one heck of a stand in.
What I Have Clients Plan For, Before They Leap
By the time we’re having a a serious conversation about leaving corporate, most clients already know that it’s about what they build before they go, so the landing is soft and not a crash.
First is the cushion. What does it cost to run your life for twelve to eighteen months with no income? This amount should be sitting in cash, ready to spend down as needed. I want clients to leave from a position of work optional, where the first year of a new venture is genuinely optional income, not required income. Desperate decisions and good decisions are rarely the same decisions. If you need to stay longer to build the cushion, stay longer. You owe it to yourself to have a real shot at what you’re building.
Second is the sounding board. Line up your study group, your mentors, your peers who’ve done this, while you still have a steady job and can be selective about who you bring in. Make sure that you have something to give / teach others and that you have something you can learn from them. Don’t put yourself into groups where you have the most knowledge. Those groups will not push you in the way you need.
Third is benefits, specifically, because it’s the piece people underprice the most. What does health insurance cost on the private market for your household? What happens to disability coverage? What replaces a 401(k) match, and what’s the real number you need to be contributing on your own to not fall behind where an employer match would have kept you. To be clear—none of this is a reason to stay. It’s a reason to leave with your eyes open instead of finding out the hard way.
There is Beauty in the Transition
I love setting my own goals. I love how fast I can move. I can have an idea on a Monday and test it by Wednesday, without a committee, without three rounds of approval, without waiting for a quarter to turn over. I can experiment, watch something not work, and discard it without it being a whole process. Not being bogged down is its own kind of beauty, separate from the financial risk or the identity questions. It’s just true on its own.
I manage my own calendar and my own travel schedule now, which is priceless to me in many ways and has been for years. I brought an assistant into my business on day one, because I know exactly where my time is best spent and where it isn’t, and having support there has kept me focused on the parts of this that only I can do. My business is growing. I make every decision in it, which is both a weight and something I genuinely love. That’s the beauty underneath the risk.
Being Transparent About Partner Support
One part that is often overlooked in both job offers and job exits is benefits.
Employed, especially in a senior corporate role, you don’t spend much time thinking about your group health insurance, your long-term disability coverage, or your employer’s 401(k) match. It’s assumed. Leave to work for yourself, and none of it is assumed anymore. You’re the one sourcing your own coverage, pricing it against the private market, deciding what you can live without and what you can’t afford to.
I’m not doing that alone. My husband and I switched places on the corporate ladder (we had a slight overlap) when he joined a leadership team at a Director level almost two years ago. He still has an employer, which means we have group coverage and a plan that didn’t require us to go shopping in the private insurance market on our own. That’s a form of privilege I don’t take for granted. Being transparent about it matters when so many narratives skip over the benefits of having a partner to lean on. In short, my husband’s benefits are holding some of the risk I walked away from.
The Both/And is Almost Always the Story.
The “I left corporate and I’m thriving” story performs well for a reason. It’s resolved — a before and after, a villain (the grind, the politics, the ceiling) and a hero (you, now, free). Gray doesn’t caption well. Nobody screenshots “it’s complicated and I’m still figuring out the financial risk and emotional swings part.” But resolved stories are usually only resolved because they’ve been edited down to the parts that resolve.
I left corporate and I’m doing work I’m proud of, building something that’s mine, on a schedule that mostly makes sense for my life. All of that is true. It’s also true that I miss the identity that came with the title, most of the people I worked with day-to-day, and building with structured support around a bigger vision.
The answer isn’t swinging to the other extreme either, some version of “actually, leaving corporate is a mistake, here’s why you should stay.” That’s the same black-and-white instinct. Leaving was right for me, for this chapter.
There’s no one-size-fits-all answer when it comes to any type of “stay vs. leave” dynamic. There’s only what’s true for your life, your goals, and your values, at this point in time.
There often isn’t an “either/or”. Instead, it’s a “both, at the same time, indefinitely”. That’s what most true things look like up close.