How to Thrive as an Entrepreneur Despite the Stress

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Making the jump from a secure corporate job to entrepreneurship in our unpredictable economy is frightening. It can bring waves of anxiety, a restless mind at 3 a.m., self-doubt and a barrage of unanswerable questions about your choices and priorities. The jump represents such a massive change that most people cross the dream of “doing their own thing” off the list and don’t even consider it. This discomfort destroys people’s entrepreneurial careers, dissuading them from taking the plunge.

As someone who has navigated this path, I understand firsthand the challenge and the mindset shift required to bring a long-held vision to life. So if you’re an aspiring entrepreneur, let me share some practical advice from my own journey.

First, really listen to your gut. If you find the idea of leaving your current situation so deeply stressful, don’t jump off that cliff just yet. It might be the right decision to wait. Instead, do a little soul-searching to evaluate the source of the fear. And consider volunteering, doing some pro bono work with another startup where your talents and skills will be valued, and you can get a sneak peek at the startup world. That brings me to my next step.

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Turn your fear into fuel

Don’t be afraid of the fear. What it takes to diverge from your typical path is the ability to harness your natural fear, specifically the fear of change, and turn it into a motivator. Fear can be converted into fuel and the drive to achieve what once seemed unachievable.

Anthony de Mello, an Indian Jesuit priest and psychotherapist, captured it correctly when he said, “We do not have a fear of the unknown. What we fear is giving up the known.”

Leaving the stability and structure of a corporate role for the unpredictability of entrepreneurship is a daunting, almost numbing prospect. This transition involves more than just a change in job title; it's a fundamental life paradigm shift. In a corporate setting, routines and established procedures provide a sense of security and sufficiency — when you’re done with your to-do list, you’ve done your job.

But in the startup world, unknowns are the norm, you’ve never done all you can do to advance your company, and success hinges on your ability to navigate uncertainties and push yourself and your co-workers well out of your comfort zones.

What does that take? A resilient mindset and an unwavering belief that you can find the right application of your core idea. The entrepreneurial journey involves frequent rejections and failures, and without confidence, these setbacks can be crippling.

The voice of experience

From my experience in leaving a major bank to launch our venture fund — as well as diving into diligence on prospective portfolio companies — I've learned that a founder’s self-belief can’t be brittle. It’s something we emphasize in the classes we teach for self-identified future entrepreneurs: You’ve got to be able to take a professional punch and get back up off the mat, again and again and again.

If you are working in corporate, your confidence could be very tied to your title, role and responsibilities within a well-defined structure. I certainly was guilty of my identity being wrapped up in my title and position. You would have thought my full name was Gayle Jennings O’Byrne JPMorgan the way it rolled off the tongue for years. But entrepreneurship doesn’t inherently come with much structure, and your responsibilities at the beginning are … everything. As the driving force of a startup, faith in your vision and abilities has to overcome the skepticism and rejection you’ll get from investors, sales prospects and potential employees. So the ability to inspire others and convey passion for your company will play a significant role in success. Basically, can you inspire people to join you in your dream, as risky, crazy, impossible and bold as it may be?

Corporate life often involves working within established systems and predictable frameworks. In contrast, entrepreneurship is characterized by a constant state of flux. The lack of fixed points on the map can be disorienting, and founders have to grow comfortable with that uncertainty and how to navigate through to get to more answers and stronger foundations for decision-making.

That ability to keep moving while managing unknowns is a tough skill for even the most successful corporate professionals. You are used to a different kind of urgency, one that has some parameters around it, internal, departmental deadlines and accountability. You can raise your hand and ask a question or bounce things around with others at the next meeting or work huddle. Not so when the deadlines and tempo are set by your clients, possible prospects or, in many cases, set by yourself because only you have the real insight into the big picture. The hustle, unpredictability and thinner resources of a startup just don’t allow for that. Founders have to embrace everything (i.e. the known, planned, unknown, unplanned, the big and the little) and be agile in their approach.

Learn to sell yourself and your vision

Departing from the corporate world will also require the ability to sell yourself and your vision. Big corporate brand names open doors and lend credibility. But you won’t have that luxury anymore as an entrepreneur. The doors that opened in the past simply because of the firm I represented or the title I held don’t necessarily open in the same way now that I’m out on my own. Now it's about my brand, my track record, my integrity, my network and the enthusiasm I can generate about what I am building. You’re starting from scratch and will have to sell yourself and your vision. This requires not only a good idea but also the ability to read audiences, pitch them effectively, listen and engage others and close deals.

One of the most significant barriers to progress for many entrepreneurs, especially women and people of color, is the need to be perfect. Perfection paralysis can be fatal in a startup. I've seen data that say perfectionists do not get more done than non-perfectionists, that they don't have higher-quality work. So, while a certain degree of perfectionism can motivate, excessive perfectionism often leads to paralysis and the very thing that entrepreneurs are afraid of — failure. The focus should be on launching, receiving customer feedback and iterating based on that feedback.

There are numerous resources available to new entrepreneurs, from books and podcasts to startup communities. Engaging with these resources can provide valuable insights and support. For example, listening to podcasts such as NPR’s "How I Built This" can offer inspiration and practical advice from successful entrepreneurs.

Transitioning from a secure corporate job to entrepreneurship is a journey fraught with challenges, uncertainties and myriad emotions. Ultimately, the journey from corporate life to entrepreneurship is not just a change in job title but a fundamental shift in mindset and approach. Embracing this change with confidence and resilience can lead to extraordinary success, fulfillment and financial reward.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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Gayle Jennings-O'Byrne is CEO of Wocstar Capital and Co-Founder of the Wocstar Fund, an early-stage venture fund using a female arbitrage strategy by investing in women of color tech entrepreneurs (“WOCstars”). Gayle (pronounced: Gay-lä) was named "10 Women Changing the Landscape of Leadership" by the New York Times (March 2021), one of the Top Black Venture Capitalists by Business Insider (February 2024) and Top 10 Women of Influence in Venture Capital by Venture Capital Journal (July 2022). Gayle has over 30 years of Wall Street and tech experience.