(“The Hour Between Dog and Wolf” was originally published on Keenan’s Substack. Read more of Keenan’s published work here.)
Many people ask what it’s like to leave your job. This point of no return is hard to describe. Of course, some have nest eggs they can live off, while others start companies without one. Every journey is different. But the paranoia that runs through your veins—the awareness that most entrepreneurs fail—is sharp. It’s not a statistical lie you can ignore, and there are plenty of horror stories out there.
But as I thought of them, I was also reminded of Bezos’s Regret Minimization Framework. Trying and failing isn’t so bad. It’s probably worse in certain countries (conservative cultures often carry bad social stigmas around failure), but living life without trying is likely more painful than trying and failing, even if society judges you. Deep down, you may earn a lucrative steady paycheck that helps you fit-in, but you’ll also be living a lie to yourself, one that can become an unfulfilled dream under the cloud of comfort and conformity.
I remember the day it happened to me. Right up until the moment I decided to go out on my own, it felt like I was hanging from a rope on the side of a cliff. I couldn’t imagine life without a job and the security blanket that came with it. But once I made the leap and that rope broke loose, I felt like a huge weight had been lifted off my shoulders. Suddenly, urgency kicked in. But so did freedom.
Mondays, all of a sudden, were exciting.
Did it mean I hated my job or my career in finance? I started to ask myself all these questions. The next was: “If I hated that world that eventually convinced me to leave, what exactly is my passion now?” The answer was unclear.
But one thing was certain: I loved freedom. And I only realized it when that rope finally broke loose. The cloud I’d been carrying for years—quiet doubts, career what-ifs, Sunday and Monday blues—finally cleared. I felt, for the first time, that I could do what I wanted, on my own terms.
That said, breaking loose has its drawbacks. As the old cloud cleared and blue skies began to appear, a new cloud started forming: financial insecurity (lack of liquidity), a fresh wave of what-ifs (including two young kids), and other unknowns. These thoughts can drive you to borderline paranoia if you are not careful.
There was no slim chance of making it. There was only one option: a 100% chance of making it. I knew the expected lifetime value of this path had to exceed my previous life. No ifs, no buts. This was a non-negotiable. A must. It’s hard to say that with confidence when the statistics are stacked against entrepreneurs.
But something interesting happens when you move from stability to instability—when you go from the safety of paychecks to the uncertainty of building on your own. Nobody really talks about this in-between stage, where you’re unsure whether you made the right decision. Because I can say that at this stage, nobody really does know whether they have. Life is not that linear to say “I have created a fixed strategy for success and I am ready.” There are too many unknowns.
It reminded me of the book The Hour Between Dog and Wolf by John Coates. How humans, like animals, shift behavior under pressure. How risk changes us. The same chemicals that fuel fear also fuel courage and sharpness. Traders get a boost of testosterone that makes them braver (which is a good and bad thing – boom-bust tendencies). Entering the venture world is similar: you go from subdued employee to owner operator and all these emotions kick in.
There was a point between those two situations that I can’t quite describe. Adrenaline starts pumping, then settling, then pumping again. You realize you don’t have safety. Then you realize it isn’t so bad after all—that survival is possible, and there’s a chance for upside. Then you go back to doubts.
This cycle continues until you have a few wins under your belt. But the waves never end. The comfort of the domesticated dog fades, and the instincts of the wild wolf return. This feeling gets even wilder when you get into the early stages of building a business.
There is a nice line by Seneca. He says “Nothing can satisfy greed, but even a small measure satisfies nature. So it is that the poverty of an exile brings no misfortune, for no place of exile is so barren as not to produce ample support for a person.”
I read this quote from one of this books, and I found it powerful. In other words, the great stoic states that it takes a lot for a person to starve. Most of us can withstand loss of wealth from a survival perspective, and I guess the consensus view is that the risk of loss and its repercussions are far greater than what reality suggests. This reminds me of the response from Jeff Bezos when he talks about risk:
Now I am not saying that the risk is really that small. Even with this belief, you still get those butterflies in your stomach.
Building a network helps. Surround yourself with people who are better than you. People you can speak to, seek advice from, and who actually listen. As you go out on your own, the more you learn from those ahead of you, the less mental strain you feel.
Why? Because your ideas get validated or challenged. Unsure of your next step? Ask someone who’s been doing it for 30 or 40 years. Mentors and access to knowledge (whether through people or even books) make a huge difference as you navigate this transition.
I often speak to corporate types, and most of them plan for the “right time” to pursue their entrepreneurial goals, but that “right time” never arrives. It’s usually tied to having a certain amount of money. But paychecks become too addictive, and as you build the habit of receiving them over time, it becomes harder to leave—especially as your salary grows and you earn more credits for your shining CV.
This is why most never make the leap.
As an entrepreneur, your CV goes out the window. I say this because that feeling of being detached from your credentials (your “ladder”) can be scary. It almost feels as if you have a chance of falling back down to the bottom.
But the upside? A chance to be a real leader with skin in the game. And the best part? Credentials don’t dictate anything. Your achievements do.
There are many arguments against entrepreneurship. No safety net. A family to support. Uncertainty. I get it. But that doesn’t mean you can’t start tinkering and testing the waters. Waiting for the right time is a bridge to nowhere. The only way to do it is to try. That part is free.
Some people argue that they’re meant to be employees for companies. Meant for jobs. Meant for structure and obedience and the path to corporate nirvana. It’s a way to justify their current situation. But over time, interests change, skills develop, environments shift, and by then, it might be too late to go on their own. That original belief starts to fade, and retirement starts to look very appealing.
And by the time they realize they could have done it, it might be too late. That’s when the idea of retirement becomes the light at the end of the tunnel. But once they get there, they start asking: now what?
ABOUT THE AUTHOR
Keenan Ugarte is Managing Partner at DayOne Capital Ventures, an independent private holding company that invests in and builds high-growth, early-stage businesses that serve the underserved Philippine mass market. He is also the Co-Founder of The Independent Investor, a media platform spotlighting early-stage companies and innovation within the Philippine startup ecosystem.