December 2023. My peak burnout.
I was sitting in an Amazon office in Santa Monica just to satisfy the new “return to office” mandate.
Everything looked good on paper. Senior Technical Product Manager. Great salary. Quarterly stock. Healthcare.
Except I kept looking for my ejection handle so I could get the heck out of there. I just needed the "perfect moment".
In my bones, I knew I was a startup person. They moved fast, built things that mattered, and took real risks. The breaking point came over coffee with a founder friend:
“Igor, your advice helped us launch our first product. When are you going to take your own advice and make the leap?”
That same month, I finally did. I stopped striving for perfection. I left AWS to start working on Yordly. Best decision I ever made.
What does it mean to make the leap?
Making the leap isn’t about quitting your job to chase some vague dream. It’s about betting on yourself when you have something valuable to offer.
For me, it meant going from stable paycheck to variable income. From AWS brand recognition to building my own reputation. From implementing other people’s strategies to creating my own.
Recently I’ve been thinking about a question that was asked at a recent webinar I helped facilitate:
“Any advice for those still on the fence about making the leap?”
Here’s the truth. You can create elaborate business plans and spreadsheets projecting your revenue. None of it matters. You have no idea what problems the market will hand you, what price you’ll actually charge, or what opportunities will emerge.
At some point, you have to decide: am I going to make a bet on myself?
Tips for your leap
Looking back, I realized that when embarking on any big journey, success usually comes down to having three things: support, skill, and courage.
So before you make that bet on yourself, answer the following three questions honestly.
Support: Activate your network
Q: Can you name 10 people who would take your call and actually want to help you?
This isn’t about having a huge network. It’s about having genuine relationships with people who know your work and would be willing to make an introduction, provide feedback, or even become your first customer.
Your warm leads should include former colleagues, industry contacts, and people who’ve seen you solve real problems. If you’ve been helpful to others in your career, this list should write itself.
In the past, I’ve built this list using AI to help me map my LinkedIn network. Ask your favorite AI assistant to help you categorize your LinkedIn connections by relationship strength and potential relevance to your service or product. You’ll be surprised what patterns emerge.
Skill: Highlight your expertise
Q: If someone hired you tomorrow, could you add real value on day one?
This isn’t about having every skill. It’s about having deep expertise in something specific that companies desperately need.
For me, it’s product management & AI implementation strategy. I’d spent years at Amazon and John Deere building AI-powered products. I’d seen what worked and what didn’t. I could walk into any early-stage company and immediately spot the 20% of AI features that would deliver 80% of the value.
Your superpower might be different. Maybe you’re the person who can untangle complex technical debt. Maybe you can build go-to-market strategies that actually work.
If you struggle to find your own superpower, you could identify your unique value proposition and tailor it further to your prospects with AI as a thought partner. Feed your resume and project history into Claude and ask it to identify patterns in the problems you’ve consistently solved across different companies.
Courage: Embrace uncertainty
Q: Can you handle 6-12 months of uncertainty while you figure this out?
This is the real test. Not financial uncertainty (though that’s part of it), but the uncertainty of not knowing if your positioning is right, if your pricing makes sense, or if you’re talking to the right customers.
Some days you’ll feel like a genius. Other days you’ll wonder what you were thinking. The critical part is staying focused and iterating when everything feels uncertain.
If you need perfect clarity before starting, entrepreneurship isn’t for you. If you can find energy in figuring things out as you go, you might have what it takes.
AI assistants can help reduce some uncertainty by providing market research, competitive analysis, and even customer persona development in record time. But it won’t eliminate the fundamental uncertainty of building something new.
How do I make the leap?
If you answered yes to all three questions, and you’ve got enough savings to survive the learning curve, then the biggest risk isn’t failing. It’s staying where you are and wondering “what if”.
There’s never going to be the perfect time, perfect skills, or perfect positioning. Most successful entrepreneurs are “good enough” at the start and figure it out by doing. And all you need is enough to start, not enough to guarantee success.
The path forward is simple: put one foot in front of the other and just go.
Ready to leap?
I’m launching a 3-day, self-paced course that shows you exactly how to find and connect with your first customers using AI.
No spray-and-pray tactics. No generic outreach. Just a systematic approach to identifying the right people and crafting messages so personal they think you’re reading their mind.
The waitlist is open and limited to 20 spots. If you’re ready to stop talking about making the leap and start taking action, this is where you begin.