How to Take Other People’s Money Without Feeling Guilty

The first time it happened, I thought I’d reached the pinnacle of pleasure.

Later, the cash just felt like paper.

Then, poison.

Can I be honest with you? I’ve been fighting a mental battle since $2.99 dropped in my bank account from my first presale of my first book. I felt like I’d won the lottery.

The magic started to die down a little after a client fired me for bad work. It melted away even more when a deal with iHeartRadio fell through. Both those times, I was panicking in a negotiation about $150 or so. Things have changed a little since then. Recently, I started a project for something like $4,500.

Sorry I did that — acted I didn’t know it was exactly that amount, and I got $1,125 up front and 15% of that will be taxed. This is part of the game people play.

It’s easy to sit on the other side of the internet and have an intellectual discussion about making money. I used to sit around with a calculator

“Look how much I could be making if I just did XYZ!”

I think that’s natural behavior. After all, it’s easier to dream than do.

What we don’t calculate is the tangible emotional and spiritual transfer which occurs alongside the exchange of funds. There is an expectation now, spoken or not, that both your life and the life of the person you charge will be better after this transaction. If misplayed, you wind up with guilt and doubt; they wind up with anger and regret.

Here are a few things that have been true if I’ve earned money guilt-free:

1. When my work is priced correctly

You’ve seen this before:

“Buy my course on marketing! It’s only $697!”

The “course” is sometimes nothing more than several screencasts and a powerpoint deck. But, with the right copy and positioning, you can sell anything. (I think today’s America is living proof of that).

I haven’t and won’t sell something for more than what it’s worth. The shame is not worth the payout.

2. When the client can afford it

If someone is giving me their last dime to accomplish for them, I don’t really want any part of it.

Could a video I’m making for them change their life and bank account? Sure. However, the pressure from dealing with a person who can’t afford what you’re offering in the first place is rarely worth it.

And when I say “rarely,” I mean “never.”

3. When I talk to Kyle

The other day, I was worried my price point for something was too high. I met with a colleague to run the idea past him, and he confirmed my greatest fear — it was double what he expected me to say.

Full of insecurity, I went crying to my friend, someone who has been selling stuff on the internet for years.

He said this:

“Calm down. Does the guy even want what you’re selling? I wouldn’t buy cat food even if it was 98% off because I do not have a cat.”

Oh, right.

Kyle is part of my mastermind group. Whenever I say something ridiculous, he puts me back on track. When I am down, he encourages me. When I doubt what something is worth, he corrects me.

And sometimes he makes analogies to cats, which is also fun.

4. When I am not an imposter

Most people who start making money on the side often suffer from Imposter Syndrome. (The ones who don’t probably should.)

Imposter Syndrome is the result of a loud fear or doubt which will not allow you to internalize your accomplishments. It often takes the form of:

  • Perfectionism
  • Overworking
  • Refusing praise (“oh, that’s nothing”)
  • Fear of being “found out” or “exposed”
  • Discounting your own work while exaggerating others’
  • Never feeling your accomplishments are “enough”

I am a chronic sufferer of Imposter Syndrome. I don’t know, maybe it came from my background — raised by two teachers, shopping at Goodwill, never eating out. I won’t pretend to know the psychology behind it.

I only know one way to beat it:

Surround yourself with other people who think you are worthy and don’t mind telling you.

A constant stream of genuine affirmation works wonders.

5. When I put money in myself

For the first years, I refused to spend any money on a project I’d been hired for. That’s money out of my pocket, right??

If it was a video project, I would search animation templates for inspiration. Instead of paying the $16 for the files, I would spend days trying to recreate what someone had already done. Often, I ended up with someone half the quality.

Now, I make it a point to spend some of my own money to contribute something new or different or fresh. I might outsource some of the things I don’t do well.

When people give you money, they don’t often care what you spend it on. They are just looking for the output to match the investment.

6. When I did what *they* want, not what I want

Imagine a scenario which you went to my boss and said:

“Hey, I know you asked me to run this report, but instead I was investing my time in learning a new guitar riff. That’s cool right? I can play it for you if you’d like!”

If this is corporate America, you still get paid, but there will likely be some ramifications. The first (and only) time I ghost wrote a book, I thought it would be a great idea to showcase some of the things I’d been learning about fitness. I would tie it in with the main themes of course. It would be a great chance to make me seem more knowledgeable.

Instead — “Todd, why did you put that there? I’m not a fitness guy.”

I did it because of ego. I forgot this was your project.

Oh, and I was trying to hit a word count.

7. When I’ve gotten rid of all the bad ideas

Part of creative professionalism is understanding probably 7 of every 10 ideas are garbage.

This is never a problem. Until, lost in the speed and deadline, you agree to implement the first idea you and your client come up with.

I write at least 10 ideas for almost everything I do. The best one is never the first one. It’s usually somewhere toward the end. It’s sometimes a combination of items 2, 6, and 12.

Sometimes, you have to go through a mountain of crap to find gold.


Here are a couple other “not” posts:


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— TB