🥷🏽 Self Sabotage: The Good Parts

I’ve been listening to books about business and personal growth over the last month and I noticed something interesting when it came to the idea of self-sabotage: the entrepreneur/hustle culture thrives on it while the more “emotionally intelligent” people regard it as a blocker to personal growth.

Well then.

Climbing a Mountain

Let’s start with the personal growth stuff, shall we? It’s a bit more positive. I read a summary of the audiobook The Mountain Is You and I was intrigued:

Coexisting but conflicting needs create self-sabotaging behaviors. This is why we resist efforts to change, often until they feel completely futile. But by extracting crucial insight from our most damaging habits, building emotional intelligence by better understanding our brains and bodies, releasing past experiences at a cellular level, and learning to act as our highest potential future selves, we can step out of our own way and into our potential.

The idea of self-sabotage is straightforward: you subconsciously do things that keep you from doing things you consciously want to do, for instance:

• Make a lot of money or get a raise.
• Start a business.
• Go on a date with someone new after a divorce or breakup.

I have suffered from this, in every case above. When success comes, I start to twiddle and optimize things, which invariably leads to bad things, like spending time writing code instead of content, or “pivoting” my side business when I don’t need to, further causing me to not create content.

On the dating front, I find myself saying things and instantly regretting it. The first date I went on after my divorce was with a wonderful person that I would happily have kept seeing. Within 30 minutes I found myself talking about deeply personal things and ultimately blurted out “you’re the first person I’ve been on a date with in almost 30 years”.

Damn. It’s hard to write about this.

The main signs of self-sabotage are:

• Perfectionism. You never feel like something is finished, so you keep at it and don’t try new things, because the first thing needs your attention. Or you say too much because you feel you haven’t said enough to get your point across.
• Uprooting. Redoing, rebuilding, reshaping — focusing on the future and “next time, I’ll do it better”.
• Pride (or stubbornness). You won’t leave a bad situation, believing you can fix it.

Each of these keeps you from focusing on the real problems of your life, apparently. I like this idea and the book resonated with me. In fact, it did more than that: it forced me to look directly at the root causes of why I do the things I do, and why I don’t see “results” with the things I enjoy doing.

So… did it work? Well, let’s see what the hustle culture says.

Broke and Up Against a Wall

I love listening to hustle books, and I know they get a bad rap from a lot of people, but I think that’s an overreaction. Yes, there are the “you gotta grind if you want it” folks out there — I don’t listen to them. And yes, there are slimy click-baiter social media freaks too, and not just in the personal productivity realm, mind you.

Anyway, here’s who and what I’ve been listening to:

• $100 Million Dollar Offers and $100 Million Dollar Leads by Alex Hormozi. This guy is the embodiment of “hustle bro”, but he’s a lot more than that, which I’ll get into below.
• Feel Good Productivity, by Ali Abdaal. A kinder, gentler approach to doing the things you want to do.
• Million Dollar Weekend, by Noah Kagan. Practical tips on how to start a side business without spending a ton of time and money.
• Atomic Habits, by James Clear. Of all the books here, this is the one that will change your life.

This list is about 1/10th of the “hustle books”, as I like to call them, that I’ve read over the last few years. Some are good, some make me cringe, but all of them have the same story:

I was broke and in trouble. I knew I had to do something, but all I had was a credit card and my friend’s/mom’s couch. That’s when a friend/parent/partner suggested …

Alex Hormozi was ripped off by a business partner and some of his customers. He was over $100,000 in debt and had just 30 days to come up with an idea… which, through trial and error, came together.

James Clear got hit in the face with a baseball bat that almost ended his baseball career. With the help of friends and family, he came up with a recovery system, focusing on small, 1% daily changes.

Noah Kagan was #30 at Facebook but got fired because he accidentally let something slip at a conference. Down and out, feeling like a failure, he struggled to find his path…

You get the idea. In fact, I would say that every single productivity/hustle book I’ve read starts off like this. Sure, there are exceptions, but the “rags to riches” cliché is still very alive.

And Then I Realized…

These stories always pivot around the Big Reveal that you can see a mile away. We all love success stories, don’t we? Reading about someone else reaching 1 million MRR within 6 months is inspiring! If they did it, why can’t we!

For one simple reason: these people live a life where they put themselves in a position with no other choice. Their backs, literally, against a wall.

Ali Abdaal wrote about this in a blog post, when he announced he was leaving his career as a doctor (emphasis mine):

I’ve had a bunch of conversations with friends and ex-colleagues thinking of leaving their jobs too, and trying to weigh up the pros and cons. One thing I’ve noticed, which is what Paul Millerd points out in his excellent book The Pathless Path too, is that we all tend to underestimate our ingenuity. We think ‘if I quit my job, and plan X doesn’t work out, I’ll have nothing to do, and then I’ll be broke and homeless and unhappy and no one will love me’. One of the main problems is the leap from ‘plan X not working out’ to ‘I’ll have nothing to do’. There’s always stuff to do. We underestimate our ability to figure things out, to adjust, to make plans on the fly and execute them.

When I lived on Kauai, people would ask me constantly: how did you ever decide to move here? That must have been hard… and, honestly, it wasn’t. My ex and I had talked about it for a year or so and then… just did it. I don’t say this in a “oh, well sure, you know me, I’m awesome” kind of way. Not at all! I had been through the Dotcom implosion and had a new child, and I was falling apart. We were young and took a chance, and everything we read about moving to Hawaii was “there is no plan, there is only the doing of it”. So we did it.

I left Microsoft in 2009 because I was struggling at the job for both personal and professional reasons. I hadn’t planned on leaving, but before I knew it, the words were out of my mouth. I was stressed out, couldn’t sleep, cranky, and my friends called me a “broken record” when I would complain. I was absolutely terrified when I quit (I had two young kids and a wife to support), but wow did I feel free. I decided to try a startup of my own instead of finding a full time job, and it worked out, thankfully. I still had to take side contracts, of course, but I found them when I needed.

So, question: are these examples of self-sabotage, or self-empowerment? I honestly don’t know.

Is This a Contradiction?

Alex Hormozi is one of my favorite authors, but I know a few people who think he’s all hustle bro. I can see why — he talks at a million miles per hour and doubles down on “if you focus on this and do these things, you’ll make a lot of money”.

The problem, however, is that you:

• Need to spend time finding an idea that people are interested in and then need to recognize when the changes you make actually work.
• Have the drive to keep going, which usually means having the support of a partner or family. Alex is quick to point out that he wouldn’t be who he is without his wife’s support.
• Have the ability to handle the success.

That’s the problem with all of the money-maker books! There’s a lot of psychology you have to get through, which is usually addressed by “go to therapy, it’s good for you, I can’t help you with that”, which is good advice. But what if you, like me, were raised with the idea that rich people are assholes? If you read The Mountain is You, you’ll come to understand that you’ll keep yourself from making money because you don’t want to be an asshole.

More than that, however, is that you have to swim in the deep end of the psychology pool if you want to build a business. If you follow Alex’s, Noah’s, and Ali’s advice, you’ll need to be comfortable with the notion of trying, pivoting, failing, and then trying again — and hope that you have people around you that can tolerate this.

This cycle of creation and evolution seems to sit squarely on top of the Perfectionism, Uprooting, and Pride behaviors discussed above. Perfectionism in that you know if you just try one more time, changing your sales copy, offer structure, or ad campaign, that this time you just might crack it. You might rebrand (or Uproot) your business during a pivot, giving your customers what you think they want. As long as you don’t give up (Pride)!

In The Mountain Is You, the author portrays self-sabotage as the thing that’s keeping you from growing. You’re focused on problems outside yourself, offering a distraction from the issues inside you. This makes sense to me.

My hustle books, however, use these exact same mechanics in a more positive way: as a way through to something better. James Clear challenges you to improve your life by doing the smallest thing you can, every day. Putting your running shoes by the door is step one to ultimately becoming a runner. Is your focus on becoming a runner a distraction from your deeper issues?

I know that I wouldn’t have what I have in this life, which I’m very grateful for, if I didn’t lean into my self-sabotaging tendencies. I know that I also could have let go a little earlier, letting that book or video course be finished, without trying to improve it and its sales copy.

I won’t end this post with an “it depends” — far from it. I recognize these forces inside me now, and my work, at this point, is not to resist them, but to let them work for me, not against me. When a book or course is done, leave it alone. Reasonable A/B testing (2, maybe 3 rounds) is a good thing when it comes to sales copy, ads, and offers. Anything more than that is diminishing returns, time to move on.

So: a contradiction? Sure, just like most things in life; they can help and they can hurt. The trick, William Potter, is not minding that it hurts.

Originally published at https://bigmachine.io on March 11, 2024.