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Quitting entrepreneurship to pivot my career in my 30sFeatured

As I hit “submit” on my first job application in nearly 10 years, I wondered if I was doing the right thing.

At 33, I was running two successful, self-made businesses. So why on earth would I hang up my entrepreneur hat and rejoin the “corporate world”? 😱

Spoiler alert: it wasn’t for the money.

For 10 years, I called myself an entrepreneur. It felt like a crucial piece to my identity. All my friends would say “You’re so lucky you’re your own boss! You get to take time off whenever you want!”

They didn’t know about the silent nagging that kept holding me back, keeping me small, disgruntled, frustrated, and well… just unhappy.

I tried everything to make my businesses work for me. I changed to a coaching-style business model, hired contractors to do the work that didn’t “light me up”, spent a small fortune in online courses that promised the holy grail. But finally, in 2021, I was unable to ignore that gnawing inside and dove headfirst into a journey that I never expected.

Through months of business coaching, therapy, journaling, and too many tear-stained calls to my sister, I came to the embarrassing revelation that my businesses weren’t aligned with my best strengths (or even interests). 🤦‍♀️

But at 33, with a never-stops-moving 3-year-old, a self-employed husband, a desire to finally build our Instagrammable, rustic-farmhouse chic new home (a la Joanna Gaines), how could I walk away from two businesses I had already built up?

🤨 Have you ever felt like you just “fell” into your career? Like you woke up one day and thought, “How did I get here?”.

For many of us, it’s been a steady progression from post-grad days. You excitedly get a job after college and one job leads to another, leads to another… all in the same line of business and you never really stop to think, “Is this what I should be doing?”.

Once I pulled back the covers on my business and realized passion and skill set just weren’t there, I had to make a change. (I’m glossing over this for the sake of keeping this short-ish and sweet, but this is a long process however you slice it.)

For me, I realized career satisfaction comes from 2 key factors:

1. Work that aligns with your skillset (Are you a talker/collaborator/communicator but spend your day entering numbers into a spreadsheet? 🚩 🚩 🚩)

2. Work that aligns with your core values (Spending time with your family or having time to workout during the day is important to you but your company offers no flexibility? 🚩 🚩 🚩)

💡 A helpful exercise to try here is to write a job description for your role (no cheating and looking at what your company provides). Put down all the technical skills, soft skills, values necessary to be really successful in that role?

Do you match up? (I didn’t.)

Once you have an awareness of what is misaligned for you, brainstorm how you can move forward. Can you craft your existing position to better fit your skills and interests? Do you have a supportive leader/mentor you can share this information with? Do you need to consider a career change?

And more importantly, how does this information change your vision of yourself and self-identity?

Letting go of my “entrepreneurial” identity was hard. Like really hard. I felt like a failure 10x over.😬

But this story has a happy ending.

Once I got my ego out of the way (I Kon-Mari’d that… thanked it for what it gave me and then let it go…), I was able to focus on next steps.

For me, that was a career change. Actually, it was a career rebirth… I happily dusted off my recruiting skills and found my dream job that aligns with my natural skill set and a company that aligns with my values.🎉

But career changes are tricky! Here are four tips that I employed to pitch myself for roles (especially when not the best fit on paper):

👉 Do the work. Research the company, create one master resume and then make copies of it and tweak it to exactly fit each individual job you’re applying for. Use their language from the job description, include numbers, stats, results as much as possible.

👉 Write a dang cover letter. Old school? Time-consuming? Yes and Yes. But this is your place to shine. Share exactly why you are applying for this job, acknowledge any disconnection and draw parallels to help the recruiter understand what you bring to the table.

👉 Focus on results. Prepare for the interview by outlining 2-3 solid examples/projects in your mind that you feel should reflect your ability to do the job well. Again - draw parallels for the interviewer.

👉 Know your tradeoffs. Find a job opportunity that lights you up? Are you willing to take a salary cut for it? Or a less glamorous title? Or have to build back up vacation days at a new company? It would be nice if everything lined up perfectly but often there will be trade-offs when doing a career pivot.

If you’re feeling stuck in your career, give yourself space to step back and reflect on your true strengths and what brings YOU fulfillment. This is a timely process. Share your thoughts with trusted mentors, cry a little to your friends, but in the end, trust your intuition.

Do you feel bold enough to share your innate strengths? Celebrate them by commenting below. 👇

(Mine: Relationship building, communication, organization, personalization, fun!)

Wow! This is amazing. I've been struggling with figuring out the career transition process and you answered every single one of my questions. Definitely can relate to the "failure" feeling with my career. I thought FOR SURE I would be a lifelong teacher, but after seven years, I realized this is just not for me. My husband is also currently making a career pivot. So... with the both of us in the midst of a transition without having the consistent stability can be scary. It's empowering and encouraging to hear others' journeys to help along the way of this process. Thanks for sharing!
You've got this Tiffany! 100% agree with the scariness. My husband is a farmer so our income isn't consistent either and that's a real hurdle to overcome as well. My only advice is to keep assessing what is the right fit for you (and also dig into why teaching wasn't the right fit) so you can adjust going forward!
Just wanted to say hey to another former educator! I was a school counselor for years before running my own business.
Hi! I'm a career exploration coach and help several teachers pivot, if you want to chat let me know! free coaching call here --> calendly.com/woken/demo
Thank you SO much for sharing your story with such transparency.! Full disclosure, I am in the business of helping women make the reverse pivot (I'm a corporate escape coach). But your experience is such an excellent testament as to why doing the deep work of discovering your zone of genius, your passions, etc. is absolutely critical for sustained entrepreneurship. People say to me all the time that they want something else, something more from their work life. But most of them follow that up with "but I don't know where to start" or "but I don't know what I'm good at." My answer is always along the lines of what you've described.Anyone can learn business operations, but building a foundation like what you've described (based on innate strengths), is the only thing that will keep you afloat over the trials and tribulations of entrepreneurship. You also stand to make a ton more money when your heart is really in it, and it's reflected in your commitment to your work. If anyone reading this needs some help gaining clarity around a career transition, lmk! I have some resources that could help.
Love your title ☺️ "corporate escape coach"
Thank you @mstucko!
I couldn’t agree more!!!
@katiespellman Thank you for your transparency and the wealth of information you have provided. Alignment is a gift to ourselves as we navigate leaving an impact in our own way! Congratulations and blessings on your new chapter.
“Alignment is a gift to ourselves…” a great motto for all things in life (not just our career!)
Thank you for sharing. I have been struggling with a career transition, going from corporate to being a full-time entrepreneur. Often I wonder if I what it takes to be this amazing entrepreneur my mind tells me to be. At the same time, I cringe at the thought of working for a large company, living in a cubicle daily. I don’t know if there is a happy medium, but your post gave me clarity on many of my questions. Thank you!
@camAndri - I don't think there is ever one "right" answer! We just keep moving forward taking the best next step (thanks Frozen 2) but I think that ability to know our strengths and check in with ourselves is so often overlooked!
There must me something in the water. 💦I can 1000% relate to you when you said, "I called myself an entrepreneur. It felt like a crucial piece to my identity". Albeit, I was a failed entrepreneur, for 20 years, I was DETERMINED to be one. In my mind, and during those years, there was no other way. But also, I didn't know what options I had coming out of college. TL;DR - I graduated as a Mechanical Engineer. I didn't discover the world & the possibility of marketing, content marketing, etc. - until almost 10 years later. And almost 10 years after that, I'm FINALLY finding my stride.And now that I have a VERY promising career in front of me, and I have some distance from the entrepreneurship kool-aid bowl (proximity changes everything), I realize that I've been self sabotaging myself by trying to identify as an entrepreneur, solely.Now that perspective has kicked in, I realize that all I needed was balance. Have a solid career, that I love, and still throw in those side hustles that I can't seem to avoid. 😅Entrepreneurship is a part of my DNA, but it doesn't need to be the dominating factor. And I gotta say, I've never felt more aligned with myself. And working for the right company? Ho-ly shit! Hello joy!So yes, girl!Get your corporate job & bypass the days when your heart skipped a beat when you see a Slack message, or email, from your tax accountant.🤣
I couldn't relate more to this! You've put my feelings into words, thank you so much for sharing this! I'm pivoting my business to fit that ideal role for myself and I'll use your steps to do that. Thank you
@MashaZvereva - yes - sometimes all we need is pivot (not even an overhaul...) I think just taking the time to do the work is so important to getting to a place of alignment :)
Thanks for sharing this. I identified with some of your processes. I was an entrepreneur for seven years, it wasn't easy to leave that identity, but finally, I did it. Then I spent three years in different roles as project manager, account manager and learning in parallel about design, coding, marketing, I confess that I felt a little bit lost because I wasn’t sure or hadn’t decided in what role to focus on until this year when I discovered that what really excites me is a product manager role… so right now I am preparing to take a formal role on that.