Part 1 of 3: Build Something Series
Is It Time to Build Something? Recognizing the Moment
In Part 3 of our layoff series, I mentioned something that deserves its own conversation: is this your moment to build something?
Not everyone should start a company. Most people shouldn't. It's hard, uncertain, and usually doesn't work out.
But.
If you've had an idea in the back of your mind - something you've been thinking about for years but never had the time or push to explore - a career disruption is a natural moment to ask the question seriously.
This series is about that question. Not a pep talk about following your dreams. Not hype about AI making everyone an entrepreneur. Something more honest: how to know if building something is right for you, what the landscape actually looks like in 2026, and what it takes to do it well.
Why Now? The Disruption Advantage
There's something that happens in a career transition that doesn't happen when you're employed and comfortable: the inertia breaks.
When you have a steady job, even one you don't love, starting something feels like an unnecessary risk. You have income. You have stability. You have identity tied to your role. Why throw that away for something uncertain?
But when the choice is taken from you - through a layoff, a company shutdown, or just a realization that you can't do this anymore - suddenly the calculus changes.
You're already in the uncertainty. You're already facing the unknown. The "risk" of starting something doesn't feel as different from your current situation as it would have six months ago.
This is the disruption advantage. Not that disruption is good - it's often painful. But it removes the barrier of leaving something comfortable. You've already left.
The question now is: what do you do with that?
What "Building Something" Actually Means
Let me be clear about what I'm talking about, because "starting a business" means different things to different people.
It might be a software product.
An app, a tool, a platform. Something you build once and sell many times. This is what I did with ReApply and FitCheck.
It might be a service business.
Consulting, coaching, freelancing, an agency. Trading your expertise for money, but on your own terms.
It might be a local business.
A restaurant, a dog walking service, a tutoring company. Something that serves your community directly.
It might be a creative venture.
Writing, music, art, content creation. Building an audience and monetizing in various ways.
It might be something hybrid.
Productized services, courses, communities. Something that doesn't fit neatly into categories.
The common thread isn't "technology" or "startup." It's this: you're building something where you capture the value you create.
That's fundamentally different from employment, where you create value for someone else in exchange for a predictable paycheck. Neither is better - they're different trade-offs. But if you've been thinking about the other side of that trade-off, this might be your moment to explore it.
The Entrepreneurship Personality (And Why It's Mostly Wrong)
There's a myth that entrepreneurs are a certain type of person. Risk-takers. Visionaries. People who were born knowing they'd never work for someone else.
That's mostly Hollywood.
The entrepreneurs I know - and I've been doing this for 25 years across six companies, plus mentoring through SBDC and SCORE - look more like this:
They noticed something broken.
Not a grand vision for changing the world. Just a problem they understood better than most people, often because they experienced it themselves.
They couldn't stop thinking about it.
The idea kept coming back. Even when they tried to ignore it, it was there.
They had some relevant advantage.
Maybe domain expertise. Maybe existing relationships. Maybe just a willingness to do the hard, unglamorous work that others won't.
They were at a moment where trying felt possible.
Severance. Savings. A spouse with stable income. Youth without obligations. Or just a disruption that made the status quo untenable.
Notice what's not on that list? "Genius." "MBA." "Connections." "Rich family."
Some of the best entrepreneurs I know started with almost nothing except a clear problem and the stubbornness to solve it.
The Honest Questions
If you're reading this because something in the idea resonates, let me ask you some hard questions. These aren't meant to discourage you - they're meant to help you think clearly.
Is there a problem you understand deeply?
The best businesses solve real problems. Not imaginary problems. Not problems you think should exist. Problems you've experienced, watched others struggle with, or have unusual insight into.
ReApply exists because I've been through career transitions, watched others go through them, and saw that the tools available were either expensive (career coaches) or shallow (resume templates). I understood the problem not because I studied it - because I lived it.
What problem do you understand that well?
Do you have any relevant advantage?
Not "can you do everything required" - nobody can at the start. But do you have something that makes you better positioned than a random person with the same idea?
Maybe you spent 15 years in an industry and understand how it actually works. Maybe you have relationships that would take someone else years to build. Maybe you have a skill that's directly applicable. Maybe you just have the credibility that comes from being inside a system.
What do you bring that someone else couldn't easily replicate?
Can you survive the timeline?
Starting something takes time. Usually more time than you think. The question isn't whether you can build something - it's whether you can sustain yourself while you're building it.
How long could you survive without income? Six months? A year? Two years? What would you need to do differently if this takes longer than expected?
Are you doing this toward something or away from something?
Running toward an opportunity you believe in is different from running away from a situation you hate. Both can work - but "away from" motivation tends to fade once the pain of the original situation fades.
Why do you want to do this? Be honest.
Can you tolerate the uncertainty?
Not "are you comfortable with risk" - almost nobody is. But can you function while not knowing if this will work? Can you make decisions without complete information? Can you handle months (or years) of ambiguity about whether you made the right choice?
Some people thrive in uncertainty. Some people are destroyed by it. Know which one you are.
The Things You Can't Know
Here's something I wish someone had told me earlier: some things you can't figure out in advance.
- You can't know if the idea is good until you try it. You can research, validate, and test - and you should (we'll talk about this in Part 3). But ultimately, you're making a bet. Smart bets are still bets.
- You can't know if you'll be good at this. Running something is different from working on something. You might love the work but hate the business. You might be great at the product but terrible at sales. You won't know until you're doing it.
- You can't know how long it will take. Everything takes longer than you think. Plan for that, but don't pretend you can predict it.
- You can't know how it will feel. The highs are higher and the lows are lower than you expect. The emotional rollercoaster of building something is hard to describe to someone who hasn't experienced it.
The uncertainty isn't a bug - it's the fundamental nature of entrepreneurship. If you need certainty, this might not be for you. If you can make peace with uncertainty, it might be.
The Different Types of "Starting Something"
Not every path into entrepreneurship looks the same. Here are some common entry points:
The side project that grows.
You build something on nights and weekends while still employed, and it gains enough traction that going full-time becomes viable. This is lower risk because you validate before you leap.
The planned launch.
You save money, quit your job, and go all-in on something you've been planning. Higher risk, but sometimes the focus is necessary.
The forced pivot.
A job loss or other disruption pushes you into entrepreneurship because employment isn't working. This is where many of you reading this might be.
The consulting bridge.
You start by selling your expertise as a consultant or freelancer, then gradually build a more scalable business on top of that foundation.
The acquisition.
You buy an existing business rather than building from scratch. Requires capital, but eliminates some early risks.
None of these is "better." They're different fits for different situations, risk tolerances, and opportunities.
My Story (Since I'm Asking You to Listen)
I mentioned I'm on my sixth startup. Let me give you the brief version so you know where I'm coming from.
I've been building companies for almost 25 years. Some worked. Some didn't. I'm a relentless builder and bootstrapper. I've had exits and failures. I've hired teams and been a team of one.
ReApply and FitCheck exist because I saw something broken in how people navigate career transitions. The intelligence that used to require expensive career coaches should be accessible to everyone. The tools available were either too expensive, too shallow, or too generic.
I didn't have a development team. I didn't have a technical co-founder. What I had was 25 years of running technology projects, understanding what needs to be built, and the new generation of AI tools that made it possible for someone like me to actually build it.
We'll talk about those AI tools in Part 2. But for now, the point is: my path into this company wasn't the conventional one. I wasn't a developer who learned business. I was a business person who is in my element when I am building.
That path is more available now than it's ever been.
The Emotional Landscape
Building something is emotionally complicated in ways that employment usually isn't.
The highs are addictive.
When something works - when a customer loves what you built, when a metric moves in the right direction, when someone says "this solved my problem" - there's nothing like it. It's validation at a level that a performance review can never match.
The lows are brutal.
When nothing works, when you're out of ideas, when you've burned through savings and it's not clear if any of this will ever amount to anything - that's hard. The isolation can be crushing. The self-doubt is real.
The uncertainty is constant.
Even when things are going well, you don't know if they'll keep going well. Even when things are hard, you don't know if they're about to break through. You're always operating with incomplete information.
Your identity gets tangled.
When you work for someone else, failure is the company's failure. When you're building your own thing, failure feels personal. This is both a feature and a bug - it drives you harder, but it can also break you.
I'm not saying this to scare you. I'm saying it because entering this world without understanding the emotional reality is a recipe for unnecessary suffering.
When The Answer Is No
Sometimes the honest answer to "should I start something?" is no. And that's fine.
If you need income stability immediately.
Building something takes time. If you can't survive that runway, getting a job is the smart move. You can always start something later.
If you don't have a problem you care about.
Entrepreneurship for its own sake, without a specific problem you want to solve, rarely works. "I want to be my own boss" isn't enough. What would you actually build?
If you hate uncertainty.
Some people are wired for the stability of employment. That's not a weakness - it's self-knowledge. Don't torture yourself doing something that conflicts with your fundamental nature.
If you're running away instead of running toward.
Hating your job or your industry isn't a business plan. What would you be building? Why would it matter?
If the timing is truly wrong.
Young kids, sick family member, crushing debt, health issues. Sometimes the right answer is "not now."
There's no shame in these answers. The best entrepreneurs I know have said "not now" to ideas at the wrong time, so they could say "yes" to the right idea at the right time.
When The Answer Is Maybe
Most people aren't at "definitely yes" or "definitely no." They're somewhere in the middle, which is actually the most interesting place to be.
If you're in the "maybe" zone, here's what I'd suggest:
Keep exploring.
Don't force a decision. Let the idea develop. Talk to people. Research the space. See if the energy builds or fades.
Do the job search anyway.
You can explore entrepreneurship while also applying for jobs. In fact, the job search process might clarify your thinking about what you actually want.
Set a timeline.
"I'll explore this for 90 days while job searching, and then reassess." Bounded exploration prevents endless limbo.
Watch for signals.
Are you excited about the entrepreneurship idea, or just dreading the job search? Does the idea get sharper over time, or vaguer? Are you doing the research, or avoiding it?
Be honest with yourself.
The goal isn't to convince yourself to start something. It's to figure out if starting something is actually right for you.
What Comes Next
If you're still reading, the question has some pull for you. Good.
In Part 2, we'll talk about the AI revolution in building - how tools like Claude Code, Cursor, and Windsurf have genuinely democratized what's possible, but also what they can and can't do. The hype is real but incomplete. The opportunity is there but requires the right approach.
In Part 3, we'll get practical: product-market fit, go-to-market strategy, validating ideas, thinking about financials. The fundamentals that determine whether an idea becomes a business or just stays an idea.
But for now, sit with the question: Is this your moment?
Not "should everyone start a company" - that answer is clearly no.
Should you? Now?
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Build Something Series
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About the Author
John Coleman is the founder of ReApply and FitCheck, and has been building companies for 25 years across six startups. He's mentored entrepreneurs through SBDC and SCORE, and believes that career transitions - whether into a new job or your own venture - shouldn't require expensive coaches or insider knowledge.