One thing nobody tells you when you start your own business: nobody is matching your 401k. There’s no HR department auto-enrolling you in a retirement plan, no employer kicking in free money every paycheck. When you work for yourself, your retirement is entirely on you.
That was a hard adjustment for me. After years of federal service with retirement contributions built into the system, running Bowles Handyman Services meant starting from scratch on that front. If I don’t set money aside, nobody else is going to do it for me.
So here’s how I’ve built my own version of a retirement plan, piece by piece.
Splitting My Money Across a Few Accounts
I don’t put all my retirement savings in one place. I use a few different accounts, each doing a different job:
Webull handles the stuff that doesn’t fit neatly into a Roth or traditional retirement account — more flexible, taxable investing outside of retirement rules. It’s the account I use when I want access to my money without waiting for retirement age, or when I’m investing in something that doesn’t belong in a tax-advantaged account.
I like having access to my money any time. When money is sitting in a 401k, it’s not really available to me — it’s like it’s in jail, and it doesn’t get paroled until I hit 59½. There are a few narrow exceptions, but for the most part, that money is locked up until retirement age, penalty or no penalty.
With my Webull account, that’s not a problem. If I hold an investment for more than a year and then sell it, the most I’ll pay federally is 20% in long-term capital gains tax — well below what I’d pay on ordinary income. (Sell before the one-year mark, though, and that gain gets taxed like regular income instead, so I try to be patient and let things sit.)
And there’s a flip side to loading everything into retirement accounts: the more you stack into a traditional 401k or IRA, the more you’re setting yourself up to pay ordinary income tax on all of it later — potentially at a higher rate than you’re paying today, once required withdrawals start stacking on top of your other income. Having money split across account types gives me more control over which bucket I pull from and when, instead of being boxed into one tax outcome down the road.
Equity Trust is where I hold my self-directed retirement account. This one lets me invest in things a typical brokerage retirement account won’t touch. It’s a different animal than a standard IRA at a big-name brokerage, and it’s given me more control over what I actually hold for the long haul.
The Roth piece of my strategy is the one I really lean on. Money goes in after tax, but it grows completely tax-free from there — no taxes on the gains, and no taxes when I pull it out in retirement, as long as I follow the rules. For someone in a hands-on trade like mine, where income can vary job to job, knowing that account isn’t going to get taxed again down the road is a real peace of mind.
Most regular IRAs weren’t going to cut it for what I wanted to hold in retirement. That’s why I opened a self-directed IRA through Equity Trust — it lets me invest in assets a typical brokerage IRA won’t touch. As someone self-employed with no 401k to fall back on, having that kind of control over my own retirement account matters. It’s the Roth side of my strategy, so it grows completely tax-free.
This is an affiliate link — if you sign up through it, I may earn a commission at no extra cost to you. I use Equity Trust myself for my self-directed retirement account.
Paying Myself First, Every Job
The habit that actually makes this work isn’t the accounts — it’s the discipline. Every time I get paid for a job, a portion of that money goes straight into investing before it goes anywhere else. It’s not a huge percentage, and it doesn’t have to be. It’s consistent.
That’s really the core of it: treat your own retirement contribution the way an employer would. Nobody’s cutting that check for you, so you have to cut it yourself, job after job.
Why This Matters If You’re Self-Employed
If you’re running your own business — handyman work, contracting, anything where you’re the one signing your own paycheck — it’s easy to let retirement savings slide. There’s always another tool to buy, another truck payment, another slow month to plan around. But the years add up fast, and a 401k isn’t going to show up on its own.
Building something like this doesn’t require being a finance expert. It just requires picking a system, understanding the accounts you’re using, and treating your own future paycheck as seriously as you’d treat one from an employer.
This post reflects my personal experience and isn’t financial advice — everyone’s situation is different, so talk to a financial or tax professional about what makes sense for you.