Let’s talk about guilt for a second.

Specifically, the kind of guilt we always feel as entrepreneurs.

Guilt that sounds a lot like:

  • I should be spending more time on my business.
  • I should have put more value into that blog post.
  • I should be putting out more videos.
  • I should be earning more by now.
  • I should be more focused on making my customers’ lives better.
  • I shouldn’t charge so much. I know people will pay it, but I don’t need this much money.
  • I should be working harder for how much I earn.
  • or I shouldn’t be working as hard considering how little I earn.
  • Why can’t I just get this right?
  • Why aren’t more people signing up for my list? I must be doing something wrong.
  • I just need to grind through it and stop making excuses.

Um, hello?

Do we never just sit back and recognize how far we’ve come and the mountains we’ve already moved? Do we forget how hard we worked to make our business happen at the level we’re currently at?

Do we so easily forget the blood, sweat, and tears of yesterday?

I know we all like to keep moving forward (it’s a great trait, really), but we’ve got to start acknowledging the work we’ve taken to get to this point.

We’ve got to acknowledge the long nights, the money spent, the stress pimples right in the middle of our foreheads, and the stomach aches from copious caffeine consumption.


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It all played a part to getting us to where we are now. It was all necessary.

Even the mistakes and the wasted hours. They taught us lessons that are carrying us forward from one great success to another.

Yet… there’s still this lingering guilt and shame that we’ve got to prove ourselves, dang it.

That we’ve got to really show them that we deserve it before we can ever sit back, rest, and truly accept it.

Like if we can’t laugh in their faces with 100% confidence that there’s no error they can find or point out about us, we can’t relax yet.

But let me tell you something: this “they” that we’re constantly competing against probably doesn’t even exist.

And if they do, I think we can all logically agree that they’re those notorious internet trolls sipping beer through a straw in their parents’ dark basement. You know, the kind of people who like to make others feel miserable about their lives just so they can feel better about themselves.

And in our heads, we know they don’t matter. In our heads, we can say “fuck them” and mean it.

But in our hearts—or maybe not exactly our hearts, but definitely somewhere deep within our chests—we still feel this quickening when someone suggests we sit back and enjoy the fruits (read:money) of our labor, don’t we?

Why Guilt Around Selling Expensive Things is BS

I get hired a lot by entrepreneurs who sell expensive products and services.

They have head knowledge that their products and services are worth every penny and that they want to earn more from them.

But once I work with them on their image and suggest that they could easily charge 2x their previous price?

You’d think I was suggesting they steal a little girl’s plush Hello Kitty toy away from her mid-play.

Their internal walls go up, their shoulders twitch in towards their chest, and and they stutter for the right words.

Because how could they possibly bring in 2x the income from their work all of a sudden?

Don’t they have to work their assess off, reach 1,000 more people, get the experience of working for a Fortune 500 company, and hustle until they cry at least four more times before they double their income?

That seems logical and fair, right?

It’s certainly what the world likes to tell us has to happen.

But let me tell you, it doesn’t.


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Case in point: my experience with an emotional healing workshop.

Earlier this month, I found myself in an emotional healing workshop.

It was one of those weird twists of fate, but I reasoned that a weekend of therapy couldn’t really hurt me, so what the heck.

The first time I saw the cost, I raised my eyebrows at it.

But then I reasoned it was actually a good deal considering the cost of therapy for the same amount of hours, but decided that it wouldn’t be for me just yet.

And then… there I was on a Saturday morning angry crying to a group of people at how unrestrictedly mad it made me every time I felt the ‘male gaze’ in public. Because fucking hell, I am not an object sent here by God for their entertainment.

And then I was talking about my childhood, and my earliest embarrassing memory.

And if you wouldn’t guess, that is not the kind of conversation I normally have around people I’ve just met.

But damn if I didn’t come out of that weekend feeling like the most peaceful version of myself I’ve ever felt.

Halfway through I realized the price could have easily been double and I’d still consider it worth every penny.

And guys, it was an emotional healing workshop. Just sit and think about how incredibly unnecessary that sounds for a minute. Especially for someone who doesn’t have PTSD or something like that.

The More You Earn, The More You Can Serve

But the thing is—with that workshop or any other service most entrepreneurs provide—the more the entrepreneur behind it earns, the more leverage he or she has to provide that service on a larger scale. (Therefore making the world a better place on a larger scale.)

Your money only amplifies the person you already are.

If you’re a good person who wants to help, you’ll do more of that. If you’re a greedy asshole who only cares about luxury items, you’ll become more of an asshole with more luxury.

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And since I’m sure I don’t attract assholes to this site, I’m going to tell you to drop your shame around selling expensive services. Or expensive products. Or whatever you sell that costs a lot and makes your bank account as jolly and fat as Santa Clause.

Because you deserve it, and so does the world.


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