YOLO! Taking the leap from a corporate job to entrepreneurshipFeatured

I’ve spent most of my life doing things as means to an end. I studied hard in grade school to get into the right prep school. I studied hard in prep school to get into the right college. I worked my a** off as a junior employee in a consulting firm in order to build up a roster of prestigious projects that would look good on my resume.

Then two things happened: I had children and I lived through a global pandemic.

Both of these things forced me to slow down and turn inward. The result was that I discovered an unsettling truth: I had been constantly living for the future, working to impress and please others, with the result that life was passing me by.

I know I am not alone in this feeling. A lot has been written and said about the pandemic-induced YOLO economy.

As Oliver Burkeman urges his readers in his wonderful book, Four Thousand Weeks: Time Management for Mortals, as we shift out of lockdown and back into the full swing of life, “take a deep breath. Ignore the deafening noise and think deeply about what you want to put back into your life. This is our chance to define a new version of normal. A rare and truly sacred, yes sacred, opportunity to get rid of the bullsh** and to only bring back what works for us. What makes our lives richer, what makes our kids happier, what makes us truly proud."

Or, as Tracy Sun (Poshmark co-founder) put it in an interview on Hilary Kerr’s Second Life podcast, “make your life decisions as if you only had five years left to live.” Why five years? Because it’s enough time that you have to think about real long-term constraints like financial viability, but short enough so that you can’t get stuck in the trap of doing things just to get somewhere else.

In my case, when I stopped and took stock of my life, I realized how much my career decisions had been driven by a desire for status and accolades, as opposed to joy and personal fulfillment. I had what on paper looked like a perfect career. I had graduated top of my class from Stanford University, gone on to study at a top-tier business school in France, climbed the ranks of an elite strategy consulting firm, and eventually landed a job as a product manager in a large Silicon Valley technology corporation.

As soon as I accomplished whatever goal I was after, I sailed right through it without stopping to celebrate, immediately focused on whatever next big thing I wanted to achieve. Sure, there were moments of fun and satisfaction along the way, and plenty of external validation, but on the whole I felt empty. This emptiness began to manifest itself in strange addictive behaviors and mental imbalance. I knew I needed to make a major change, but to what?

Some people are lucky enough to feel they have one true calling from a very young age. But most of us don’t have it so easy. We have many competing interests, and it takes us time to figure out what to focus on. To make matters worse, we suffer from collective FOMO and commitment phobia. We hedge our bets. We go into management consulting because it “keeps our options open.” We fail to commit fully to anything because it’s scary. Add to this the social pressure to do and be certain things, or the very real financial constraints of needing to pay a rent or mortgage, and most of us end up feeling downright lost. So we give away our agency and take whatever job we get recruited for.

In my case it took 3+ years of coaching, meditating, journaling, questing and experimenting in order to dig beneath all of the layers of accumulated busllsh** and get back in touch with my intuition and my truth: that I am a creative, an entrepreneur, and a champion of women and mothers. I was closest to it very early in my career (I started out working as a social entrepreneur in women’s health and microfinance) but the more I got caught up in the career rat race the further I got from it.

A few months ago, I finally worked up the courage to quit my job and start my dream company, Hera Los Angeles, making ethical luxury clothing designed for motherhood. Now, I anxiously await the arrival of Monday mornings, because it means I get to work again. I come to my desk every morning energized and excited about what I am going to learn and create, and that energy buoys me through the rest of my life.

Unlike anything I have ever done before, I don’t care whether I succeed or fail, because nothing you love doing is ever a waste of time. Ironically, I truly believe that I have a better chance of succeeding in this pursuit than in my former corporate career, because doing something you love gives you a tenacity and persistence that cannot be sustainably faked.

So how can you, too, do what you love, right now? Every journey is different and yours will be unique. I encourage you to allow it to unfold in whatever way it was meant to. That said, here are some of the things that helped me to get to where I am today:

1. Get in touch with your intuition. The only way to uncover what you truly love is to turn inwards. Find quiet times during the day when you can meditate on the question. Write down your thoughts in a journal. Go for long walks in the woods. Find a friend or a coach who is willing to listen without judgment (I worked with Anubha Kothari and cannot recommend her enough). This phase can take time. Be patient and persistent in your questing. Look for patterns in what you uncover: these are the clues that you should build on.

2. Forget what other people think. Is there something you love doing, but that you are avoiding, because you feel it is somehow not worthy? I find this to be very common among women. We tend to feel our interests are not as legitimate as traditionally male pursuits. For instance, many women have an interest in beauty or fashion, but society tells us these things are frivolous. On the other hand, no one is criticizing men for pursuing truly frivolous tech startups. Let me ask you, do you think the world really needs another scheduling app? Maybe that thing you love doing is exactly what the world needs from you.

3. Talk down fears. Most people are afraid to do what they truly love. In many cases, the fear is legitimate. It could be fear of failure, fears around financial feasibility, fear of judgment. My greatest fear was financial uncertainty. I was terrified of letting go of a regularly monthly paycheck. I am still terrified of watching my bank account dwindle as I lay the foundations for this business, but the risk is worth it. I am investing in myself and my dreams. What better way to spend my hard-earned money?

4. Find role models. The thing that tipped the scales for me was when I started listening to Hilary Kerr’s Second Life podcast about amazing women who had left corporate jobs to start thriving internet fashion companies. Like me, these were often mothers with no extra time or energy to spare. Like me, they had stable corporate jobs in which they felt bored or stifled. Like me, they had little to no experience or connections to the fashion industry. And yet they built thriving businesses. I thought: if they can do it, so can I.

5. Prioritize doing over planning. This piece is key. Once you have a strong suspicion about what it is you would like to pursue, just start doing it. Don’t overplan and get stuck in fantasy-land. The stars will never align. The time is now. Figure out some way to work it into your schedule (hint: this will involve intentionally deprioritizing other things that often feel very important) or just go ahead and take the leap. There is a whole stinking pile of advice out there about how and when to quit your job (“not until you can’t keep up with sales” or “once you’ve proven your business model”) and I call bullsh**. I think you get out of something what you put into it. So if you know what you love and you can afford to make a go of it, go all in, and you’re much more likely to end up with a viable business.

It’s too early to say how things will work out for my new business venture. Maybe I am in the honeymoon phase and the joy will fade over time. Maybe I will fail to turn it into a viable business and be forced to return to the corporate world. Life is uncertain. All I know is that I am happy now. I come to my desk every day with a spirit of curiosity and joy, rather than stress and striving to succeed. I believe that if I continue to prioritize joy, and a focus on process rather than outcome, my journey will be a much more fulfilling one.

Thanks so much for the feature Elpha team!
Thank you for sharing your story with us!
Thanks so much for sharing your journey !! I think a lot of us here and around the world have gone through something similar but you’ve been brave enough to do it and follow your path. I wish you much success and joy :)
Thank you! My intention is to inspire more people to take the leap
Inspiring !
β€œget back in touch with my intuition and my truth” THIS! thank you for sharing your inspiring story. Wishing you all the success, happiness and fulfillment with your latest venture!
Thank you Michelle
Thank you so much for sharing. I am going through this right now and this has helped me tremendously!
I'm so glad to hear that. It's not easy. The transition was VERY rocky and scary, but I am so happy I did it.
3. Talk down fears! Strong word and much needed. Thanks for sharing your story.
Fear keeps us in our boxes. I believe it is our strongest barrier to freedom. We are our own worst enemies.
Cool to hear this update Elena! You and I chatted at the very beginning of the pandemic and I think right before you began this journey. Love that you are following your dreams!
Yes I remember Stephanie - that feels like ages ago
This is so honest, thank you for pouring your soul and sharing this with us. Although, I didn’t climb that high in the career, I also left my corporate job as I felt so unhappy. Wishing you nothing but the best in your journey ✨✨✨
I loved hearing about your journey! I took the same leap almost 10 years ago...I had to go back to the corporate world after my startup didn't succeed BUT now I'm getting ready to dive back into the startup space again. My failure doesn't feel so much like a loss anymore. I feel seasoned, more mature, recharged and ready to take it on again. Thanks for the unique perspective and best of luck with Hera. I'll be following along.
So cool. Yes I think sometimes going back and forth is necessary and that's ok! Do you feel that you were able to get a better or more interesting corporate job by leveraging your startup experience?
YES! I tool the leap from corporate finance (to startup) and then was able to get into digital marketing/ecommerce with my startup experience. I would have never been able to make that transition without starting my own business. My husband and I joke that my failure in my startup opened up more opportunities for both him and myself. He now is the CEO of a successful financial services startup through a connection made in my time as a startup founder while I went back to work in the corporate world. It wasn't always an easy journey, in fact, it's been a roller coaster of a ride but I'm not sure I would change our journey.
Thanks for sharing your story @elenabridgers. I quit a comfortable corporate career late 2019 to start my own business so a lot of what you wrote resonates with me. The fear that shows up before making the decision is a very real thing. But so is the boredom that accompanies a career that you overstayed. Congrats on launching Hera Los Angeles!
Thank you. It’s still very real! How are things going?
Great so far. I'm a coach for people who are navigating their career 'first'... career change, returnship, managing people, leaving corporate to become a solopreneur. I get to be there when my clients are making their first big career move. Rewarding and purpose-driven work. Exactly what I was missing before :)