Fifteen Months In: Light at the End of the Tunnel?

I did the thing you’re not supposed to do.

About a month ago, I pulled the final string of my original plan — I liquidated an old 401k to buy myself a few more months of runway.

In my world, the world that I come from, that’s a cardinal sin. You don’t touch retirement accounts. Ever. But it was the move I needed. Alongside an honest conversation with my wife about restructuring our household finances, it bought me time. Time until November, when the next decision point hits.

So… where do things stand fifteen months in?

The Numbers, Then and Now
At my last big check-in (the 12-month update), I admitted that the business had only turned $2K in profit over a full year. Painful — like running a marathon and realizing you only moved a mile.

Now? The most recent 12 months show ~$200K in revenue and $20K in profit.

Better. Encouraging, even. But is it enough to justify the risks — cashing out a 401k, reshuffling our household, and disrupting my family’s day-to-day? That’s the question that lingers when the lights go out.

The Emotional State Check
The cliché is true: working for yourself means more hours and less pay. But here’s the part I used to roll my eyes at — sometimes it doesn’t feel like work at all.

The physical grind still takes its toll, no doubt. Yet when I’m home and a lead comes in, I get a jolt of energy. Hours vanish. I’ve even found myself explaining to my kids that being on the computer is something I want to do, not something I’m trying to escape.

And those thoughts about going back to corporate? They’re fading fast. I like who I’m becoming. I like this work. I like the flexibility. And I like that it keeps me moving — even keeping me in shape.

The Pipeline Problem (and Progress)
Our close rate still hovers under 20%. Not great.

But here’s the shift: we’re getting repeat events from the same clients. That tells me we’re making a dent. And I haven’t even turned up the heat on email and text marketing yet. That’s still sitting on the shelf.

Evolving Identity
Most of my work right now is with homeowners hosting private events. Their gatherings are too small for the big rental companies, but too demanding for side hustlers who aren’t responsive or organized. It’s a niche I don’t mind serving — though the recurring (or reoccurring) revenue opportunities are few and far between.

What I’m not chasing are the giant tent jobs. If you’ve never seen one of those installs, picture cranes lifting frames into place and forklifts crawling around like ants. Those crews may as well be building houses. That’s not the hamster wheel I want to build.

Instead, I’m leaning toward building a lifestyle business — something sustainable, not something that consumes me.

But I also know this model has limits.

For my next shot at entrepreneurship (and there will be another), I want to chase something more scalable. The events business eats time, effort, and capital before you see much movement. In the world of AI, I can’t help but feel there are far more lucrative opportunities.

Ironically, though, AI is also why I think events will matter more than ever. As automation takes over, people will crave in-person connection. We’ll want more analog in our lives. And that’s why, for now, I still feel like I’m in the right space.

The Next 90 Days
November is coming fast. Our family has some big, potentially life-changing events on the horizon, and truthfully? I’ll be just as surprised as you when it’s time to decide. I’m watching the numbers closely, and I want to keep pushing down this path — but I’m not naïve.

What’s certain is that I can’t keep going much past November on our current revenue. And yes, there’s still one last string I could pull… but I really, really don’t want to.

I know momentum takes time. But at the end of the day, this business is tables and chairs — not rocket science. I’ve got mentorship, I’ve got the resources. Which means the spotlight turns inward: if this doesn’t work, it won’t be because the path wasn’t there. It’ll be because I couldn’t walk it.

Wondering if the next 90 days will prove if I’m finally hitting my stride… or just stalling before the fall.

The Path Forward
So here we are: fifteen months in.

The revenue’s higher. The profit’s finally moving. And for the first time, the work feels less like a burden and more like something I’d actually choose.

But will it be enough to carry this into a true second chapter? Or will November be the month I have to face the hardest choice yet?

For now, I’m still standing. But I can’t shake the question: am I standing on solid ground… or quicksand?

Until next time
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