5 Stupid Mistakes I Made Doing Freelance Work (And 5 Things I Nailed)

5 Stupid Mistakes I Made Doing Freelance Work (And 5 Things I Nailed)
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Most of us cringe thinking about some of the stupid mistakes we’ve made with our freelance work over the years, but it’s all part of the learning process.

I dislike examining, let alone sharing, the mistakes I’ve made, but in the interest of others learning from my mistakes, here it goes.

Here are five stupid mistakes I made doing freelance work, followed by five things I did right:

  1. Not looking for my next job while I still had one.

Unless you’re planning to take a chunk of time off between jobs, it pays to be putting out feelers for your next job while you’re working.

I neglected to do this on several occasions and regretted it when I was off for longer than I wanted.  As freelancers, we need always to keep up contacts and plan our next move.

I regret not doing this, and it cost me.

  1. Turning down a job that was a sure thing because I thought I had another job lined up.

Sometimes as freelancers, we may get calls for jobs with start dates that aren’t locked in yet.  It’s happened to me quite a few times, and I made the mistake of passing on a perfectly good job with a definite start date in favor of one of these uncertain projects.

You can guess what happened.  The start date kept getting pushed, and I was hanging around waiting when I could have been working.

You can bet I didn’t make that mistake again.  You know the saying: A bird in the hand…

  1. Skimping on spending for footwear.

If there’s one thing we need for working on set, it’s well-made, comfortable shoes.  I wore inexpensive sneakers for years because I didn’t want to spend the money for better-made, more expensive shoes.

As I now have foot problems, I regret that decision.

You can read my review of Orthofeet shoes, an excellent brand with good support that I find comfortable.

  1. Putting up with unacceptable behavior on set.

Yes, things have changed a lot on set in the past few decades, and antics that were once tolerated are now taboo.

Abusive behavior is never okay, and I wouldn’t tolerate it on set today.  I wouldn’t accept the ‘keep your mouth shut and do your job’ mantra many of us followed in the past, and it was a mistake to allow it back then.

At least with freelance work, we always move on to the next job, but we all deserve a safe, respectful workplace on whatever job we’re on.

  1. Not getting professional tax advice early in my career.

I thought I was saving money by using tax software when it first became popular, but now I realize I probably missed a lot of deductions, spent far too much time, and ended up not saving money at all.

As freelancers, it’s worth the money to pay a competent CPA who understands freelancing and knows our industry.

I should have done that sooner.

Things I did right:

  1. I attended as many networking events as possible.

I’ve always enjoyed in-person networking events, so I had no problem attending as many as I could.

The connections I made at these events helped build my career.  We have the advantage of online events now, too, so even shy types can jump in.

If there’s one thing we need for freelance work, it’s contacts, so my advice is to network as much as you can.

  1. I took advantage of opportunities for continuing education.

I get numerous notifications of seminars, webinars, and panel discussions with industry pros, and I’ve always tried to take advantage of at least some of them.

Our industry is constantly changing, and we need to stay abreast of new developments.

With so many free or low-cost opportunities to learn, I feel fortunate to have been able to learn things that benefited my career.

Plus, it’s another chance to network with peers.  Win-win.

  1. I had at least one other income stream.

Freelance work can be scary in that it’s often unpredictable.  The unpredictability is much easier to take when we have another revenue stream as a backup.

I’ve found it also takes my mind off the industry work that can be all-consuming to the point of eclipsing everything else.

My sidelines made me money and helped me focus on something other than work.

  1. I kept a good record of business expenses.

I stayed organized with recordkeeping, so I wasn’t scrambling at tax time.  With all the recordkeeping software available today, it’s easy to keep organized.

Our careers are businesses, and we do well financially to treat them as such.

  1. I lived within my means.

We’re pretty much guaranteed to have downtime as freelancers.  Living within our means gives us freedom in what can be an uncertain industry.

There were times I wanted to be working and wasn’t, but it never devastated me financially because I always lived within my means.  I had a roommate to help keep expenses in check for years, so I never panicked when I wasn’t working.

Living within our means is one thing we can control as freelancers.


Freelance work is challenging, but we can control plenty of things in our careers, not least managing our time and money.

What things are you struggling with as a freelancer and what things are you doing right?

Let me know in the comments section.  We can all learn from each other's successes and mistakes.






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