How I handle GUILT as an entrepreneur

(And father, husband, dog owner etc.)

Hello G-blasters!

First of all, how are ya? I never ask. My wife gets mad at me for not asking how she is, or how her day was. So I’m trying. How are you? How’s your day going?

How Are You Doing Season 6 GIF by Bachelor in Paradise

Now, back to me and my thing. (I’m a narcissist, I guess. Fuck.)

Anyway:

Today, I wanna talk about an emotion that has been a huge part of MY life, and seems to be fairly universal if you’re not a psychopath:

GUILT.

Deny Kad Merad GIF by CANAL+

Me whenever I’m alone with my thoughts.

I feel guilty ALL. THE. FUCKING. TIME:

  • guilty for working too hard

  • guilty for not working hard enough

  • guilty for not being rich yet

  • guilty for caring so much about money

  • guilty for being strict with my daughter

  • guilty for spoiling her

  • generally just being a terrible father

And also, for:

  • getting mad at my wife

  • occasionally drinking too much (which these days is anything more than a drink and a half)

  • not thinking enough about other people’s needs

  • not going to the gym (feeling this one right now)

  • eating anything that makes me feel bad

  • occasionally watching porn (sorry mum)

  • wasting time on YouTube and LinkedIn

  • being on my phone when I walk my dog

  • not meditating

  • not practicing my guitar

  • not practicing my Mandarin

  • not having already bought my mum the ability to retire, and a car and a trip to Asia

Im Exhausted Already GIF by Golden Globes

You, reading this list.

… I’ll stop there to be respectful of your time and sanity.

So, why haven’t I snapped yet?

A couple reasons:

First off, I’m Jewish (weird time, I know).

Second, I’m a parent (where my sleepy people at?).

And third, I’m an entrepreneur.

All three of these identities seem to be inherently tied to an outsized feeling of guilt, of being inadequate in some way. So I have a lot of practice.

With that, here are my 3 methods for dealing with GUILT as an ENTREPRENEUR:

1. Learn to distrust my negative emotions

One of the most powerful things I learned in therapy:

Negative thoughts are most often LYING to you.

Anxiety and depression DISTORT your thought patterns, and end up telling you things that FEEL true, but are actually not.

(BTW I have anxiety and depression. I think most of us do on some level, but that’s another conversation)

Here’s’s an example:

Guilty thought:
“I’m a terrible business owner.” (I have this one daily).
Reality:
My business has grown almost every year in revenue (except for 2020 😕). I’ve been able to make a living doing what I love, and now I have a consistent stream of leads wanting to work with me and great testimonials from 100s of happy clients.

So, whenever I have a guilty thought like this, I remind myself to think of the objective reality, or at least a rational counterargument to that thought.

It’s become a habit for me by now, and it really helps.

2. Prioritize family over business

One thing I’ve heard, over and over again from successful people:

Their biggest regret is losing relationships with their spouse/kids.

Whatever my struggles with finances right now, I’m betting that more money but worse relationships with my wife & daughter will not help me feel better about life.

So when I feel guilty about BOTH working too hard AND not working hard enough, I’m going to choose to put family first where possible.

This is already paying dividends at home. And the money will come.

3. Open up to other entrepreneurs

A lot of advice for entrepreneurs is:

“Create a community of other founders and business owners, because they get it.”

And this is true, BUT:

When entrepreneurs hang out together, there’s still a performance happening:

Trying to put a positive spin on our business, that everything is going great, even though we may be losing it on the inside.

Im Fine GIF by MOODMAN

The most healing conversations I’ve had with other entrepreneurs is when I’ve broken this facade, and told them how scared or overwhelmed I am.

They ALWAYS respond with: “I’ve been there.” OR “Me too.”

Someone has to open up first, and it may as well be you.

🙏

THAT’S IT for this week! I really hope you liked this one, I struggled with cutting it down cause I have a lot to say on this subject.

Please REPLY if you’re struggling with this kind of guilt, OR just to say hi.

Also PLEASE SHARE this email if you know anyone who would like the Greenblast!

I love you all ❤️

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