I Cashed Out My Retirement Twice. Only One Still Hurts

I've cashed out a retirement account twice in my life. Twenty years apart.

The first time I was in my early twenties, and I did it for nothing. New apartment, new clothes, stuff I didn't need. Paid a penalty to the IRS for the privilege.

The second time, I was trying to keep a business alive, and it was the last money I had.

Here's the part that still gets me. Financially, the first one was the bigger mistake by a mile. But the second one is the one I still feel. And the reason those two aren't the same thing is the whole point of this post.

The First One

Let's go back to the late nineties. I was working for a corporation from eighteen to twenty-one, and they had a retirement account. I put money in. Not a lot — I wasn't making a lot — but I put money in.

Then I moved to Atlanta. I showed up in this city with a thousand dollars cash, a bed, and some clothes. That's the whole list.

I went into the service industry — restaurants. And here's the detail I actually love about that version of me: I used to keep CNBC on at work all day. Twenty-one years old, running food, watching the ticker crawl across the bottom of the screen. I wanted in. I was trying to save every dollar I could, which wasn't much, but the habit was there.

And then I cashed out the retirement account.

Not for an emergency. Not for rent. I wanted to set up my apartment. I wanted some new clothes. I was new in a city, and I wanted to look like I belonged in it. So I called, I closed it out, and the IRS hit me with the early withdrawal on top of the taxes.

You know what I told myself? It's only a few thousand dollars. I'm twenty-one. I've got forever.

That's the mistake. Not the money. The sentence.

When you've got a few thousand bucks in a retirement account, it doesn't feel like a retirement account. It feels like a rounding error. What am I going to do with that? That's not retirement money; that's a used car.

Except that was the foundation. That was the thing everything else was supposed to sit on top of. You don't get to ten thousand without going through five. You don't get to a hundred without going through ten. I threw away the bottom of the staircase and then spent twenty years wondering why I couldn't reach the top.

Every Dollar You Put Away Is an Employee

Here's how I think about it now, and this is the part I wish somebody had said to me at twenty-one.

Every dollar you put away is an employee.

I don't mean that as a cute saying. I mean it literally, because I've actually built companies. When I started my beauty business, I ran it on the side — before six in the morning and after six at night — for two solid years before it was big enough for me to go full-time. And when I finally did, I was the fourth full-time employee at my own company. Fourth. I know exactly what it feels like to not have enough hands.

That's what a small account is. It's a small team. Four people can't produce much. It's slow, it's frustrating, it doesn't look like anything yet.

But every dollar you add is another person on the floor. And unlike a real company, these employees don't quit, they don't call out, and they show up every single day whether the market's green or red. They just need time.

At twenty-one, I looked at my little team of a few thousand, and I thought, this isn't a business. So I fired everybody.

If I'd left them alone, that crew would have been working for me for close to thirty years by now. Compounding on top of compounding. That's the number I don't have and never will.

And before you write that off as a broke twenty-one-year-old who didn't know better — I did a version of the exact same thing at forty-one. With real money. When I absolutely did know better.

The Second One

My first business was called CurrySimple. I was importing product out of Thailand. And I loved it. It was my baby; it was the first thing I ever built, and I still believe the idea was good. If you handed it to me today, I could make it work.

But I didn't know business back then. Starting in 2008, the currency went the wrong way on me. Here's what that actually means: I'm buying in Thailand and selling in America. Every time the dollar got weaker, the exact same product cost me more to bring in — but my price on the shelf here didn't move. Same box, same customer, less money in my pocket on every single order. And there was nothing I could do about it from Atlanta. It was a fight I didn't know how to fight.

Meanwhile, the market was falling apart. So the retirement account I'd been feeding for about five years — never maxing it, just putting in what I could — was already cut roughly in half before I ever touched it.

And I touched it. In 2009, I closed it out. It was the last lifeline I had. It went to keeping the business breathing and keeping my mortgage paid, because at that point it was pick one: an empty retirement account, or lose the house.

I didn't tell my family. I didn't tell anyone. I was embarrassed. It was painful. You've got this thing you built, you're telling everybody it's going great, and quietly you're liquidating the last account you own to keep a dream alive that's already dead.

And here's the thing: cashing out wasn't even the real mistake. The real mistake came earlier. I held on two extra years trying to save something that was already gone, because it was my first business and I couldn't let it go. If I'd cut it loose when the math first turned, I'd have walked away with a lot more, including that account.

That's the lesson that cost the most. Knowing when to stop.

Tuition, Not Failure

Quick one, because it matters. In 2011 I started a food truck. The food truck scene in Atlanta was brand new, and the regulations were all over the place. Held onto it for about a year. Lost money again.

But that one taught me something the losses before it didn't. I looked at what I was doing and thought — why am I fighting this hard to sell an eight-dollar sandwich when I could be selling a three-hundred-dollar wig?

Same effort. Same hours. Completely different ceiling.

That's the thought that started the hair business in 2013. So I don't count the food truck as a failure. I count it as tuition.

And that shift, from low ceilings to high ones, worked faster than I expected.

The Confession I Could Leave Out

Which brings me to the part I could leave out, and I'm not going to.

By 2018 I wasn't broke anymore. That's the whole confession. The problem wasn't that I didn't have money. The problem was I still didn't have a plan for it.

In my personal account, I had AMD and Tesla. I was trading in a bull market, having a great time, with no real plan. Sold both way too early. Those two positions alone, if I'd just sat on my hands, would be worth millions today.

On the business side, we'd saved up over a hundred thousand in cash, and we bought land because the plan was to build a warehouse on it. We ended up buying a warehouse and retail location in 2022 instead, so that land is still sitting there. The whole area's changed around it. It's in our back pocket now — maybe condos someday. Not now.

So look at where the money went that year. Personal brokerage. Land. The business. Real estate.

Now count how many dollars went into a retirement account. Zero.

That's not a story about being broke. That's a story about never once thinking long-term with the accounts that exist specifically for thinking long-term. Nobody did that to me. I just didn't think that way yet.

Where That Leaves Me at Forty-Nine

About five years into rebuilding. I max a traditional IRA now. I'm not going to show you that account, and I'm not going to tell you the number — some things stay mine. But it gets funded every year, and it gets funded first now, not last.

And I'll tell you something that surprised me. I'm not actually unhappy about how this went.

Because the real estate wasn't a mistake; those are real assets we picked up before prices ran, and that's a retirement too — it just doesn't live in an account with a tax code wrapped around it. I took a different route. It was bumpy, it was expensive, and there were stretches where I had nothing.

What changed wasn't that I got smarter at picking investments. What changed is I started building systems. Making actual plans instead of reacting to whatever was in front of me. Playing a longer game than the next twelve months.

In a perfect world, I'd have been funding those accounts since I was eighteen. Untouched. Thirty-plus years. I'd be somewhere completely different right now. I didn't have anyone telling me that, and I'm not going to pretend I figured it out on my own either. I just eventually got tired of learning it the expensive way.

So I'm not sitting here telling you what to do. Your situation is nothing like mine. But if this post does one thing, I want it to stretch the timeline in your head. Stop thinking about this year. Start thinking about the thirty.

Because the team you hire today is the only one that gets thirty years to work.

If this one hits, the companion to it is my asset location breakdown — that's where I show you what my accounts actually look like today, and why most of my portfolio is still sitting in the wrong one. It's the other half of this story.

Watch the full video above, or on YouTube: https://youtu.be/_N_tvEH18fc