The Finances

“It must be nice to be able to afford to quit your job.”

I’ve heard this more than once. And yeah, it is nice to have F-You Money and I highly recommend everyone get this point. But getting there didn’t happen overnight. I didn’t win the lottery and walk into my boss's office like a baller, slam my letter of resignation on the table, and flip a double middle finger in the air over my head as I strutted out. I also didn’t get a fat inheritance from some long-lost uncle Ed. (No Uncle Ed here...don't worry, not wishing him dead.)

What really happened was decades of smart financial habits, combined with a short period of intense, deliberate planning. That's how I got to the point that I could comfortable leave the cushy job to explore the unknown.

A Foundation in FIRE (Financial Independence Retire Early)

I’ve always been into personal finance: blogs, books, podcasts. I've read a dozen or so finance books, significantly more blogs, and listened to more podcasts than I can count. My original goal? Retire at 50. That’s what I saw growing up: my grandfather retired at 50, my dad before 55. So I thought, why not me?

That meant living below my means, maximizing savings and investments, and making good decisions daily. But don’t confuse me for a frugalist. Although some people call me cheap, I’ve never set a budget. I've tried but hated it. We traditionally would buy what we want, pay off the credit card monthly, and live well. But I also pack lunches for my whole family each day, we cook dinner at home most nights, make coffee before work, and we keep recurring costs like internet and utilities in check.

But...I drive new cars. A cardinal sin of any FIRE enthusiast. I have literally always had a car payment since I graduated college, and not because I am a car buff. I like the reliability and the new tech every couple of years, and I don’t want to spend any time at the repair shop. But even then, I have almost always traded-in my vehicle and received more money from the dealer than what I owed on it, putting that money into the purchase of the next. We all have our things. This is mine.

Shifting from Accumulation to Autonomy

Originally, my investment strategy was simple: mix of mutual funds of topics I liked, without any consideration of cost. That changed after reading The Simple Path to Wealth by JL Collins. I shifted everything to total stock market index funds with much lower fees (VTSAX baby!). Later, I evolved again following Paul Merriman’s take on the Efficient Frontier for a more diversified, optimized approach. I probably did this too late honestly, but I did it when I was comfortable with our portfolio size and its trajectory.

We maxed 401(k)s for at least the last decade but honestly I don't remember when that started. We even went into after-tax contributions some years. That’s great in theory, but it left me wondering last year: were we now stuck in the Middle-Class Trap?

It hit me hard when I realized I was throwing half my salary into the stock market - putting my employment eggs in one basket (my employer) and my investments eggs in another (the market). So I started to question, was that building freedom or just locking up money I couldn’t access? Especially if I needed it before traditional retirement age. I realized I needed assets that paid me without punching a clock. Real estate never thrilled me, although I had explored it for years. But buying businesses? That got me fired up. Working for myself? Sign me up!

Planning the Exit

When I got serious about leaving the W2 world to pursue business acquisition full-time, I started stockpiling cash. We backed off 401(k) to only investing to get the full company match, and stopped investing in the after-tax brokerage accounts, but kept the HSA for its triple tax benefit and flexibility in retirement.

My wife was nervous at first. And rightfully so. This was a big change and a real departure from the traditional path. But we spent months talking and built a plan that satisfied both of our concerns. It wasn’t an overnight agreement, but a series of shared decisions that made the leap feel less risky and more of a natural next step for us. To really see how the finances could play out, which running out of money was her biggest fear, I built a simple Excel model to address the scenarios we were worried about:

No income from me: how long can we go?
Cutting spending by 25%: how does that extend the runway?
What if she lost her job too?
What if we went into “COVID lockdown mode” spending in case of emergency? We didn't spend much during the first few months of COVID lockdown, it was wild!

When I planned the exit through these Excel scenarios, I made sure we had over a year of runway based on our current lifestyle. That didn’t factor in a business down payment though, it was just our baseline. I knew the longer it took to find a business to acquire, the less money I would have for that business. But, I wanted enough time to experiment, iterate, and even fail a little without our life going sideways and that's why a year looked good to me: you can do a lot in a year.

With that, we concluded it was financially safe. Not risk-free, but risk-managed.

Healthcare and Safety Nets

One of the major safety nets: my wife kept her job. That means we still have health insurance and a baseline income. If things got really tight, we could technically survive on her income alone. It would not be fun though or remotely easy. It would mean cutting out a lot, such as cutting our saving for our son’s college and many of the comforts we enjoy, but we could make it work for a short period of time. Knowing we had that fallback made this even more of a calculated risk.

Mindset and the Moment

I wasn’t scared of leaving a job without another source of income lined up. Honestly, I knew that if this didn’t work, I could always get another job (yes, easier said than done, I know). And also, I couldn't see myself pursuing business acquisition any more with other employment obligations, I had tried that. We’re also not in the era where multiple employers or resume gaps are red flags either, so the resume gap year didn't scare me. People reinvent themselves all the time, and many hiring managers view that kind of boldness as a strength. For me, the real shift came when I started seeing continued employment as the risk and not the safety net. Staying in a job that paid well but didn’t align with my values and interest and didn't provide a diversified source of investments outside of the market was the bigger gamble.

In case you have an amazing pitch for me...I have zero interest in NFTs and crypto so those are off the table as alternatives to stocks. Thanks.

Evolving the Plan

Since the jump, I've added some income with a consulting gig and I am expanding Radio Chatter’s product line to see if we can increase revenue. That extends the runway some. We’ve also reduced discretionary spending by 25% which helps, but it hasn't been long enough to know if that is sustainable.

But one challenge keeps surfacing: time. Business acquisition takes time. And while you’re searching, your cash is slowly draining. That means the longer it takes, the smaller your potential down payment, especially if you’re targeting a larger business. I knew this risk going into the journey but it has become more obvious when looking at businesses and knowing how long it takes to find and acquire one.

So now I’m back to scenario planning:

What if I sign a purchase agreement tomorrow knowing it still takes a few months to get a loan, will I have the funds ready for that down payment? What does life look like between now and then?
What if I have no income for many months post-acquisition and we used all our money for the business?
What happens if the business needs capital soon after acquisition and I used all the money for downpayment?
What’s our max acquisition price (down payment really) we could afford while keeping an emergency fund? Should we even keep an emergency fund during this time?

The Bottom Line

Yes, it is nice to be able to quit a job without another lined up and to be able to afford the luxury of doing so. But it wasn’t a spontaneous decision. It was a calculated move, rooted in decades of discipline and designed with intentionality. You can do it too with the right mindset and determination.