9 Surprising (And Necessary) Things I Learned When Leaving My Corporate Job

9 Surprising Things I Learned When I Left My Corporate Job


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May 22, 2024 at 11:2AM UTC

So, you’re thinking of quitting your job in the all-caps Corporate America World. 

If your career until this point has consisted primarily of corporate roles, it’s natural to feel a little nervous before making this leap. Working in corporate comes with certain headaches and some unspoken rules that you may be looking to move away from, sure. But it also comes with a sense of security and, oftentimes, clearer pathways to advancement than the less-structured spaces beyond its (beige-carpeted) walls. 

Plus, it definitely stands to be noted — some people just really enjoy working in the corporate world. And for those individuals, that’s wonderful! But given that you’ve clicked into this article, we’re guessing you might not completely be one of them. Or maybe you’re simply interested in seeing what else is out there, and that’s totally OK, too.

To help ease your nerves, we heard from individuals who have experience with making this kind of transition. They shared the No.1 lessons they learned leaving corporate America – and what they would (or wouldn’t) do differently next time. 

1. Not everyone is going to support you — and you’ll need to find the ones who do.

“Friends, family, colleagues may think you're crazy for leaving a good paycheck and the career you worked so hard to build. They may roll their eyes because you're ‘pursuing your dream’ and try to talk you out of it,” Meaghan Thomas, who left her corporate marketing job early last year to start Pinch Spice Market alongside her partner, said. “Don't listen to them. These are their own fears and insecurities talking.”

Thomas recommends “surrounding yourself with people who are supporting you,” as well as looking for others who are making life choices similar to yours. Whether you find them on social media or through local business groups, these people, she says, will be a bedrock. 

“You're going to need to talk to someone who understands what you're going through, and not just your partner or best friend,” she said. “There's plenty of ‘oh sh*t, what did I do?!’ moments. You need someone to help you put it all in context and bring you back to center. A good person for that is someone who has had their own ‘oh s*t moments’ and gotten through them.”

2. There is no “right time” to leave.

“There is NEVER a right time,” Heather Hakes, formerly an executive in the oil and gas industry and today a mindset coach, said. “You may never feel ready or have all of your ducks in a row. Do it anyway. The regret of not trying weighs way more heavily than actually doing it.” 

3. Yes, your skills are transferable!

“Your skill DO transfer to other environments,” Alex Hinrichs, a former Microsoft exec and today a consultant, said. “When you're in a big corporate environment for a long time, the fear is that you learn skills that only apply in your company. It's great to learn firsthand that it's not true.  Problem solving, leadership, ally building, communication — those skills are universal.”

4. Vertically isn’t the only direction you can grow.

“Aiming higher isn’t always the answer. While I learned a lot at the corporation, it came with a sizable mental toll. I was happier overall at other positions and ultimately became an entrepreneur,” Holly Rollins, President at 10xdigital and a former corporate marketing exec, said. “Once on the entrepreneur track, I have certainly experienced stress but it’s under more of my control.”

5. Outside of the corporate world, your resources will probably feel limited in comparison.

“I previously worked with one of the largest law firms in Canada; it was a very corporate job, with a very corporate compensation package, and I had a very corporate life. It was an easy decision to leave the field and start in entrepreneurship; however I did learn a valuable lesson regarding resources,” Michael Alexis, today the CEO of TeamBuilding, said. “At a large firm, you have everything available to you: abundant access to template documents, case files, partners to consult with, and even unlimited coffee. On your own, you often start from scratch. Doing the work may take you three to five times longer as you build from scratch, so you need to focus on building up those templates and resources. Doing so will allow you to become much more efficient over time.”

6. The way you experience drive and ambition may change, possibly for the better.

“Without the security of the steady paycheck, or the “golden handcuffs,” I have to make sure I’m constantly meeting my goals, learning, growing, and working on my mindset,” Maria Akopyan, a divorce attorney who left a corporate law firm to start a divorce coaching practice, said. “The entrepreneurial drive is more primal than the desire to obtain promotions or bonuses in a corporate job. It literally is survival mode. Whether the business succeeds or fails depends entirely on my mindset and output. For me, this is more exciting than anything I had experienced in the legal field.”

7. You’ll need to become a master of self-accountability.

“You, and only you, have to hold yourself accountable,” Carmen Ventrucci, a Founder and CEO who left her corporate job to launch True SISU Life, said. “In the corporate life, there is always someone there, assigning priorities, tasks, projects, yet when you're your own boss, you are truly your own boss.  While this is extremely liberating, it can also be extremely new.  This is a mindset shift for many and took me a few weeks to get used to.  I lost time building my business because I failed to shift my mindset fast enough and was still waiting for other people to tell me what to do, and  in reality, there was no one there to do that.”

8. You are more than your job title.

“I've always been obsessed with my resume and the roles I've acquired,” Sonya Matejko, today a writer and communications consultant, said. “For a long time, I associated myself with what I spent 40+ hours a week doing. The morning after I got laid off from corporate, I remember lying in bed asking myself, ‘Who am I without my job?’ Then I remember walking in Central Park until I found the perfect bench to sit on, and I journaled for hours about who I was and who I wanted to be — all this on a Tuesday afternoon while the rest of the world was hustling.” 

Matejko says she realized she’d never given herself the time or space to think about these things — and now, recognized the potential in herself that she’d been holding back on.

“I was more than my job title. I was more than my resume. I was more than I had given myself credit for,” she said. “And outside of corporate, I didn't need to wait for an annual review to remind myself of that. It was up to me to remind myself daily: you are enough.”

9. Even if you love your corporate job, it’s still OK to want to try something new.

“I learned that even if I never wanted to leave corporate before and LOVED working in corporate, it was totally fine to change my mind and want to leave,” Nicole Coustier, an Executive Performance and Life Coach who left her role as an exec at a consulting firm in 2017, said. “Both could be true at the same time: that I loved my corporate experience, and that I wanted to leave it.”

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