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This mistake cost me $105K/year

Don’t wait until you feel like climbing.

I was in a lot of pain. I didn’t want to do it.

Last Saturday, we celebrated my oldest son’s birthday by heading out to a local wildlife zoo. He loves animals and requested the trip.

As we kicked off the day, I tried hard to mask my crabbiness. My right hamstring was aching badly. I misjudged the heat of the day and wore jeans. There was a ton of walking and I’m out of shape.

But I’m trying to bring my best to my family, so I put on a happy face and we honestly had a great time.

In the middle of the long and winding trail through the zoo, we came across a tall pole with hand and footholds on the side of it, running all the way to the top.

My son, being 9, immediately jumped onto it and climbed a couple of steps up before getting nervous and climbing down.

My other son, 6, wanted to try, but was too scared to bother.

I thought it would be fun to try, but I was really uncomfortable physically.

I shook off the complaints, grabbed the metal holds, and started climbing without saying a word.

My family went crazy. They loved it. My boys cheered. My wife led my daughter in a “Yay, Daddy!”

I climbed all the way to the top, patted the top of the pole, and climbed down again.

Once my feet hit the ground, my 9-year old ran over and climbed all the way to the top himself. And my 6-year old even got on for a few seconds, took a couple steps, and then asked to be let down.

Sure, I could’ve just walked past it. Nobody asked me to do it this time.

But look at all the good that happened because I decided to do it:

  • I proved a little something to myself
  • I got a tiny bit more exercise
  • I motivated my boys to take another shot at it and try harder
  • I gave everybody a little memory and some fun energy into the day
  • I got past my bad mood
  • I gave myself a little fodder to write this essay

I didn’t feel like it.

But I did it.

And now I reap the rewards.

This attitude gutted my business

In 2014, I made $140,000 as a freelance copywriter. It was my best year up to that point.

And I got lazy.

I assumed the clients would always be there. The money would always be there.

I didn’t actively grow my business. I didn’t go out and get clients aggressively. I took my foot off the gas.

Why? Because I didn’t feel like working harder.

I wasn’t in the mood.

I was doing fine without it.

Fast forward to 2017, and I made just $35,000 in copywriting that year.

That’s a $105K loss in annual income in just a few years. Brutal.

Waiting until you “feel” like it is the perfect way to destroy your chances of regular, stable income in this line of work.

How to keep your foot on the gas…

You know how many people tell me that outreach isn’t “fun”? That it’s “painful”? Or they “hate” it?

Guess what? I agree.

But I do it anyway.

And that’s because I know what it’s going to take to stay in business, keep the lights on, and keep food on the table for me and my family.

Here are a few tips to keep yourself motivated, even when you don’t “feel” like improving your business:

  1. Stay humble. If you have the luxury of not having urgency thrust upon you right now, always remember that it can happen at any time. You can lose income FAST and suddenly. Be humble enough to recognize that you are always vulnerable and should keep moving forward.
  2. List out the benefits of moving forward. Some of those benefits of climbing the pole that I listed above? Those were going through my head when I was considering it. Often, you just need to SEE the benefits in front of you to get your butt in gear.
  3. More importantly, focus on the COI (Cost of Inaction). Play the “What if?” game. If you don’t keep moving forward, and you do wind up losing income suddenly, what happens? How far behind will you be? How painful will it be, financially or professionally? Think of yourself in 6 months – will you wish you had done more outreach now? The surest way to avoid regret is by imagining it and feeling it NOW… so you can take steps to avoid it proactively.
  4. Have a simple, efficient game plan. You don’t have to market yourself aggressively if you’re busy and you have plenty of income. I’m not saying you should be consumed by MORE MORE MORE. I am saying you should always nudge your business forward, even if you just do it incrementally. A clear, intentional game plan is invaluable to have in your pocket at all times.

It’s a common trap

Many freelancers work with zero sense of urgency.

These are the same freelancers that will be frantically posting “DMs are open – ready to work!” on LinkedIn and X the moment they lose a client.

Don’t be them.

Stay urgent and have a plan to keep moving forward in good times and in bad.

Once I developed that plan, my income went from $18K to $99K to $250K+ per year.

And the “roller coaster” stabilized.

You want the dream life of a freelancer? Then put on your hard hat and make sure you’re working to grow your business a little bit every day.

Don’t wait until you “feel” like it.

Because you never will.



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