In 2021, Thomas Kelly stood at a crossroads in his career journey.
Already a successful family doctor in his early 30s, the more sensible choice was clear: pursue a certification in vascular surgery. But that isn’t what Kelly did. Instead of doubling down on his medical profession, Kelly quit his secure practice to pursue a new path in artificial intelligence (1).
Luckily for Kelly, his AI bet paid off. According to the most recent funding rounds, Kelly’s company, Heidi, has a valuation of $465 million.
As an AI scribe, Heidi’s system helps medical providers organize their days and transcribe notes on the spot to reduce many necessary but tedious tasks. The idea behind Heidi came from Kelly’s own frustration with the limited time in his daily practice.
When explaining why he decided to give Heidi his full attention, Kelly told CNBC, “[I thought] I’ll regret it forever if I don’t take this chance. How many surgical trainees are good enough in math and have had business experience and can build this product? I think not many.”
Although Kelly focused on medicine during his studies at the University of Melbourne, he also had a passion for math and computer science. Plus, he had previous experience building the AI system Oscar, which helped thousands of students practice interacting with a lifelike medical interviewer.
“Maybe it was hubris,” Kelly admitted, “but I thought if anyone can start this company, it would be me, and let’s try and see what happens.”
Is quitting the smart career move?
Many physicians in the U.S. can relate to Kelly’s struggles in providing quality care to patients while taking care of their own mental and physical health. An analysis from Stanford found that approximately 45% of physicians reported at least one symptom of burnout between 2023 and 2024 (2).
Add in the recent headlines related to AI startups raising millions or billions (3), and it makes sense that some of these burned-out professionals would think about making a similarly bold career move. While Heidi shows that it’s possible to be successful as a tech entrepreneur, statistics suggest this kind of success is the exception rather than the rule.
On average, 70% of new businesses fail within a few years, and this figure is even higher in the AI sector, according to Exploding Topics (4). Data from marketing agency Digital Silk shows that 90% of AI startups fail, and just 5% of generative AI companies generate any positive return on investment for their clients (5).
So, instead of increasing financial independence and creating a worry-free life, becoming an entrepreneur is more likely to increase stress. Many surveys suggest entrepreneurs have burnout rates similar to those of other professions, and these worries are compounded by extra financial burdens (6).
Again, that doesn’t mean taking a leap can’t be the right move, but Kelly’s story shows how crucial it is to have transferable skills if someone wants to experiment with new financial paths. Since Kelly already had knowledge of computer science and experience building a real-world AI product, he was in a stronger position when entering the competitive AI space.
Any burned-out employees who are seriously considering becoming an entrepreneur need to recognize that it takes just as much work, if not more, to leave a predictable profession. The harsh reality is that success with a new business is rare and not easily replicable.
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Taking a practical pause before a permanent decision
So, if becoming an AI entrepreneur isn’t realistic for some of today's burnt-out professionals, is everyone just stuck in the never-ending stress cycle?
Not necessarily.
Entrepreneurship isn’t the be-all, end-all strategy to addressing burnout, nor is it the most practical option. But one lesson everyone can take from Kelly’s story is to leverage transferable skills when searching for new opportunities.
For instance, considering side projects or advisory roles could be safer ways to experiment with new income streams without going all-in on a high-risk and irreversible decision.
If someone still has a strong entrepreneurial spirit, they first need to plan their financial and personal costs for long-term sustainability. Besides setting aside enough savings for at least a few months of living expenses, consider the impact of this new project on family obligations and mental health.
Don’t forget that there are other ways to reduce the risk of starting a new business without completely cutting off a more reliable income stream. For instance, some founders might negotiate part-time work or take a sabbatical that preserves income while pursuing a new direction.
When transitioning into uncharted career territory, it’s equally important to set explicit “stop-loss points,” or predefined times to reassess progress and call it quits if certain milestones aren’t met.
Dealing with career dissatisfaction deserves a thorough, honest evaluation, not an impulsive, romanticized escape. Rather than leaving a stable career to build a startup, test assumptions early and design change in a way that keeps options open in case things don’t work out the way you intended.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
CNBC Make It (1); Stanford Report (2); Fortune (3); Exploding Topics (4); Digital Silk (5); Zipdo (6).
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Eric Esposito is a freelance contributor on MoneyWise with an interest in financial markets, investing, and trading. In addition to MoneyWise, Eric’s work can be found on financial publications such as WallStreetZen and CoinDesk. When not researching the latest stock market trends, Eric enjoys biking, walking his dog, and spending time with family in Central Florida. Eric holds a BA in English from Quinnipiac University.
