5 stupid financial mistakes I’ve made as a freelancer (and their consequences + how I’m fixing them)

Photo by Vitaly on Unsplash

Just a normal guy here, folks. I’ve been freelancing video and film production for 10+ years, and have made plenty of mistakes. Here’s a few of the bigger ones, their consequences, and ways I’m trying to fix the problems I’ve caused for me, my family, and business.

1. Not budgeting

As the kid growing up who saved almost to the point of miserliness, I guess I never really felt like I needed to budget. Not launching into life before getting married also didn’t help.

My form of “budgeting” was a naive and convoluted thought process involving analogies with ponds, rain, and waterfalls.


Constant frustration for my wife, who taught herself how to budget on a shoestring. Ambiguous and ignorant spending habits for a long time after getting married (we’re coming up on our 4th anniversary, and I’m really just now grasping what solid money management looks like). Lack of prioritizing Life Right Now first and even more lack of laying out & following the little steps to achieve goals.

The fix:

Since I’ve been full time freelancing for 6+ years, one reason I avoided budgeting was that it seemed too difficult to nail it down when income varies so much. But expenses are usually easier to estimate or lock in, so my wife and I were able to find a system that works really well for us.

2. Saying “no” rarely

There was $28,000 in my bank account when my wife and I got married. No debt. I’ve never carried debt. So I thought I was responsible with money (saving + debt-free = responsible).

But I had no idea how much life costs.

Not that I became frivolous with money, or said yes to everything. But far too often instead of saying “no, this doesn’t fit into the budget right now” or “no, we need to save this money for the slow season”, I’d find a way to make things work. They always did of course. Because I was responsible, kinda.

That $28,000 saved in the bank was almost gone within 10 months. Having very little work in that year was partly to blame. But we were trading rent for property maintenance, had only the two of us to feed, and very few expenses. Example: we ate a lot of raw cheese that year ($14+/lb.).


$28,000 savings gone in a year for no good reason. Failure to save money (really, actually save) for 2+ years after that. Allowing our lifestyle to grow with income instead of saying no.

The fix:

Say no. Ask the budget if I can spend this money. If the budget says no, I say no. Is there a savings category that has money for this? If yes, can the expense justify touching that savings? If no, then I say no.

Also, no doesn’t have to mean no forever.

3. Not setting aside 30% of each paycheck for taxes

Freelancers have to pay estimated taxes every quarter. I learned this early, thankfully not the hard way. But what I did learn the hard way is that a $1800 paycheck is not a $1800 paycheck. It’s a $1200 paycheck.

For years, I’d try to put aside my estimated tax amount when I thought about it. If I thought about it.

The consequences:

Too often it’d be June 1 or September 7 or January 13 (the April date is easy to remember because the big tax month) and I’d be scrambling money around to make sure I could pay.

Quarterly tax payments aren’t exactly fun to pay, but I made them far more stressful than they should have been.

The fix:

Transfer 30% of a paycheck after depositing. Right away. A mindset shift also helps. When looking at my incoming invoices/monthly projections, I have to remember that nice fat number is a lot thinner than it looks.

4. Letting lifestyle expand to fit income

It’s easy to do. A lot of it goes back to failing to say “no” often. And a lot also comes from failing to realize and own the reason for living well below our means — short term sacrifice to take steps right now to get to goals and dreams down the road.

When we got married, I had just moved to southern Illinois (nowhere close to Chicago), thinking I could dominate the video production market there since literally nobody else was trying to hit the quality level I aspired to. Maybe there was a market, maybe there wasn’t. I bought a $3000 cinema camera (BMCC 2.5K FTW!) a couple months into living there, because of course I had $20k-something in the bank, so why not?

Or take 2016. We managed to hit the six-figure mark (barely, before taxes). While we did save a $1000 emergency fund and put a few thousand into a famine fund for the next slow season, I also expanded our budget and said yes to a lot more things. When you’re seeing $8000-$10,000 come in during a month, why not?


In southern Illinois, maybe I could have spent that $3000 to hire a part-time marketing intern (I suck at selling). Then with the flow of work resulting from someone doing something I can’t do very well (find & generate leads), I could have legit hired someone for marketing & sales, bought the cool camera, and made our super-low-expense lifestyle work. Instead, I had a super cool camera, no work, and a dwindling bank account. And scared wife.

In 2016, I could have built our savings back to pre-southern Illinois levels and beyond no problem. But instead, I settled for less saving, more lifestyle, and struggling through an unforeseen extended slow season that was coming. With a wife and two children. A scared wife (the kids are too little to be scared).

The fix:

Make the budget. Stick to the budget. Say “no.” If the budget says no, I say no. Keep the end goals in mind, and especially the steps to get there. It’s okay to expand budget in appropriate ways (i.e., I know that our current $350/mo food budget isn’t realistic long term with a two-year-old boy who can pack the pancakes).

A budget is made to be kept, not fluidly adjusted from month to month.

5. Failing to set or stick to both personal and business financial goals

Big fail here. I often am guilty of having BHAGs (you know, Big Hairy Audacious Goals) and depressing myself because I can’t connect here to there. Like trying to grow a video production business but not opening my mind to simple concepts like hiring people to do the stuff I suck at doing. So because of the disconnect, I fail to set or even see those first or next steps I can take that will incrementally lead to what I want.

This disconnect, combined with failing to say “no” leads to a lot of other problems, like allowing lifestyle to expand with income.


Cycles of feast or famine, because I don’t set myself up for success by making a path to achieve the plan. Failing to grow. Failing to achieve goals like saving or having money to invest in my business or idea.

The fix:

Thinking through dreams, goals, desires, interests. Listening to my ultra-realistic wife’s voice. Thoughtfully laying out a path to those dreams that keeps my family and values intact. Admitting I’m selfish, then focusing on others instead (because selfishness doesn’t help achieve goals). Switching to an incremental success mindset, being committed for the long haul. Sticking to the budget.

Almost four years after launching into life, I’m 27 and just now beginning to take an actually responsible mindset toward finances and other goals. Hope these thoughts have helped. Let’s keep learning.

To learn more about me or see my work:




Studio website

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