Both/And, NOT Either/Or
A Practical Guide to Pursuing Entrepreneurship During Financial Uncertainty
582 Days
As of this writing, that is how many days it has been since I had a full time job. A lot of things have happened in this time. We've had the summer Olympics, Luigi became a very popular name while the US healthcare system did not, two NFL Super Bowls have happened, and of course we elected a new president.
And now with another year almost halfway done it seems like I am up against a perfect storm of things happening; the current state of the economy, the massive amount of tech layoffs since COVID, and what brings my writings to you today: the fact that I'm currently caught in a particular crossroads of where the hell I think I am supposed to go with my career.
Which brings me to a middle of the week beautifully sunny day in Pleasanton, CA where I had the privilege to attend the East Bay Small Business Development Capital Summit. My "schedule" was pretty open so I figured why not attend and learn a little more about what kind of interesting information they could offer for a wanna-preneur such as myself.
Upon me pulling into the large parking lot where the conference was being held, I could see a lot of individuals still sitting in their cars, as if almost psyching themselves up for what they were about to go face. Many people of all ages and races were congregating towards the entrance, many dressed up in nice suits or professional wear as I start walking up looking more like Hunter S. Thompson.
Still, those slowly churning gears of my aspirational self wanted to be able to explore the idea of what it would actually take to start a business for myself. I was getting nowhere fast in terms of securing a job in the particular field I came from so in a way, the idea of starting a small business for myself could be my own way of taking the power back.
An Unexpected Goldmine
I expected a stuffy conference room with droning voices about projected earnings and market strategies. What I found instead was something closer to a support group for people equally terrified and exhilarated by the prospect of building something from nothing.
The first pleasant surprise was the sheer volume of free resources available to small business owners. Not just pamphlets and websites, but actual human beings from the SBDC and various lending institutions who seemed genuinely invested in helping regular folks navigate the nebulous process of business creation. At first appearance, these lenders didn't seem like vultures looking to squeeze desperate entrepreneurs; but instead spoke and acted like sherpas offering to guide climbers up a treacherous mountain.
"I've been there," said one of the banking representatives, speaking of his own experience working in his own family's restaurant before going off and what he does today. Because of this camaraderie of sorts, you could tell there was a level of empathy being communicated to the audience at large.
Another pleasant surprise was while I was wandering between booths, I happened to run into an old associate of mine, Shawn Flynn, who I first met at the Create the Future Summit last year. We caught up briefly, and I suppose I had made enough of an impression that he invited me to attend his upcoming CTF conference as a "journalist." Apparently, my Hunter S. Thompson aesthetic was working in my favor.
One business card exchanged; one door unexpectedly opened.
But perhaps the most valuable moment came when a dedicated SBDC staff member offered to personally review my own business plans – mostly a series of wildly varying documents and half-baked PowerPoint slides on my own productivity system and consulting business I had in mind. His offer to help didn't feel like a chore but instead an opportunity to learn something new. Hopefully they have seen worse. Much worse.
The Vision
582 days gives a person a lot of time to think. During this involuntary sabbatical, I've crafted a vision for myself and something I actually want to build: an organization focused on sustainable business practices and meaningful productivity tools. While I'm still working through the details and legal structure, the core concept revolves around helping businesses transform their operations with people-first design and environmentally conscious technology solutions.
But alas, visions don't pay mortgages. And the Bay Area has a particular talent for draining bank accounts with a vicious efficiency, next to almost none. Still, my wife has been heroically shouldering our financial burden, but our savings account resembles a bathtub with a pulled plug - circling the drain with alarming speed.
The urgency is real: two small children who inexplicably need to eat every single day, a mortgage that refuses to pay itself, a car payment, and the countless other financial tentacles that wrap themselves around life in one of America's most expensive regions.
And of course, I know I am not the only one going through this.
The most surprising takeaway from the Capital Summit wasn't about business at all - it was about the strange optimism permeating the small business community, particularly here in the Bay Area. Despite economic headwinds around tariffs or no tariffs, in addition to cooling tech hiring, that make the news sound like a horror podcast, many of the attendees spoke about their own opportunities with conviction that bordered on religious fervor. It was really inspiring to see so many out there willing to take such a risk.
And so here is what these lenders could offer: Anything from a microloan could be enough to build a decent website and establish a minimal presence and a more substantial loan - let's say around $250K - could potentially fund a co-founder, marketing efforts, and even a small team.
The Reality
The math still terrifies me. But for the first time in a long time, it doesn't seem entirely impossible. And like any bank, a loan is exactly what it is; they expect some up front capital in order to get a loan, which they expect you to pay back with interest so it's not like, "oh well, business failed so I guess that's it for the loan payments".
Bills must be paid and children gotta eat. In the meantime, I've been exploring job titles I previously would have scrolled past - coordinator, analyst, even physically demanding warehouse work. Pride is a luxury I can no longer afford. Even half of my previous salary would keep our household functioning while I build something on the side.
The sensible path forward seems increasingly clear: build incrementally while maintaining some form of income. Start with one aspect of the business - perhaps the IT consulting for seniors, which requires less upfront capital - while working a job that covers our immediate needs.
As I listened to other entrepreneurs share their stories at the summit, I noticed a pattern: many had started with something far simpler than their current operation. They hadn't launched fully-formed businesses; they had planted seeds and nurtured them while tending other gardens.
These weren't stories of all-or-nothing gambles. They were testimonials to patience, persistence, and pragmatism.
The Next 582 Days
As I drove home from the Capital Summit, the late afternoon sun casting long shadows across the freeway, I felt something that had been absent for months: a plan forming. Not a desperate fantasy or a worst-case scenario, but an actual, viable path forward.
Step one: Secure some form of employment, even if it's not my dream job. The family needs stability.
Step two: Schedule that meeting with the SBDC advisor to refine my business plan, focusing initially on the most accessible part of my vision.
Step three: Explore microloan options for getting a professional website established.
Step four: Build in the margins - evenings, weekends, lunch breaks.
I don't know what the next 582 days will bring. The economy might improve, or it might crater further. My dream business might take off, or it might evolve into something entirely different. I might find unexpected employment that reignites my passion for working within an established company.
What I do know is that the either/or thinking that has paralyzed me for months - either find a job OR start a business - is a false dichotomy. The entrepreneurs I met aren't fearless risk-takers; they're strategic builders who understand that sustainable success rarely happens overnight.
And perhaps most importantly, I'm not alone in this journey. The rooms full of people at the Capital Summit - from the lenders to the advisors to fellow entrepreneurs - form an ecosystem designed specifically to help people like me navigate this precarious path.
So here's to the next 582 days. May they be defined not by what I've lost, but by what I'm building. One calculated step at a time.