Self-Sabotage Starts as Armor
Wait, this thing I hate about myself is trying to help me?
About 35 minutes into the Zoom call, I was attacked.
“So how many people have you reached out to since the launch?”
I squirm in my faux leather chair from Wayfair. I already don’t like where this perfectly reasonable line of questioning is going.
“Probably ten or fifteen people,” I mutter.
“Are these strangers, or people in your network?”
It’s the chair. So uncomfortable. That’s why I’m still wiggling.
“No, all warm connections.”
“Would you even charge any of them, if they did want to do it, since you haven’t had any sales?”
It’s decided, I’m buying a new goddamn chair when I hang up.
“No,” I say with a deep sigh, “probably not. I need testimonials for anybody to believe in this thing.”
Silence.
The guy on the other end is my coach, a good buddy of two decades who is also building his 2nd Act. He’s helping me untangle my shit so I can better help you untangle yours. He’s also a really nice New Yorker.
I’m a less-nice New Yorker, now waiting to see if the nice guy is gonna rough me up.
He does. Nicely.
“So, why do you think you’re playing small here?”
My memory of the call gets a little hazy after that question, likely because in the moment, I was doing what I do best: bullshitting.
I’ve been recruiting since the first year of Obama’s first term. You can wake me up with a bucket of ice water at 4AM and I’ll be able to freestyle an engaging conversation.
Ten minutes later, I hang up with my tail between my legs and go about the rest of my day, blissfully ignorant of the roadside explosive that was just buried in my mind.
Six or seven hours later, the kids are finally in bed. I’m journaling. Usually, my pen starts off by scratching out some top-of-mind bullshit until I make my way into the depths.
Instead, I’m looking down at a page that has one sentence written across the top:
WHY ARE YOU PLAYING SMALL?
Boom.
This is Your Brain on Self-Sabotage
The diet that you stick to until you start losing weight...and then you’re raiding the kid’s snacks while you’re on the couch at night watching Succession.
The course you purchased to learn a new skill...that’s sitting at 67% completion in Skool and would require a password reset to access.
I don’t need to describe self-sabotage to you. You don’t flinch at my examples because you’re too busy cringing at your own annoying patterns.
But you’re successful. You’ve gone after goals and hit them. You’ve achieved some level of status, financial gains, or competency that proves you can go get shit done.
Which makes the whole thing even more maddening.
Self-sabotage is when you know exactly what to do, you have the knowledge, resources, the capability...and you still don’t do it.
Dr. Ryan Sultan, Assistant Professor of Clinical Psychiatry at Columbia, defines it as “the internal conflict between wanting success and fearing it, manifesting in procrastination, self-doubt, and other self-limiting behaviors.”
To which I say: “I’d appreciate it if you’d stop reading my goddamn journal, Doc.”
You’re not confused or under-resourced, and you don’t need more information. You’re filling a pool with a garden hose and leaving the drain open.
Your brain’s primary job is safety, not growth. Self-sabotage is a protection mechanism that’s outlived its usefulness.
When forward motion looks like a threat, whether that’s to your sense of belonging, safety, love, or self-worth, the brain will sabotage the move. It’s doing what it was built to do (even if the behavior has the look and feel of a cockroach).
Think about yourself like a house. Your foundation is a concrete slab, poured during your childhood. The rest of your life is built upon whatever was mixed in during those early years.
And, let’s be real, we’re all a little fucked up. We all had something (or more likely, multiple somethings) while we were growing up that taught us early rules. If I do X, I lose Y. Maybe Y was love, or parental approval, or the phone call to let you know the buddies are getting together. The concrete was poured, and it dried fast. Childhood ain’t all that long.
Now, decades later, every time you try to move, the rule fires. You’re gonna quit the job. You’re gonna start the business. You’re gonna ask someone for money for what you built.
And then...you just don’t.
And when you look into the mirror at night, you have a tough time holding your gaze.
Killing My Own Launch
I just went through this a few months ago. The launch of my 2nd Act Launchpad program lived somewhere between “underwhelming” and “humbling.” I built a page on my Substack, wrote a post, recorded the launch video (my first video), pushed it to my socials...and that was about it.
A few friends checked it out. A few good friends gave me really valuable feedback.
Nobody else gave a shit.
Of course, hindsight makes things obvious. The kind of obvious that makes you say, “I know you’re working on your positive self-talk and all, but seriously? You missed THAT?”
I wasn’t sending DMs to everyone I know about this thing to see who they knew.
I wasn’t recording MORE videos to keep getting the word out there.
I didn’t even have a proper landing page. I made it hard to find what I’m selling. “Yeah, that shop hidden behind the loading dock. That’ll be perfect.”
What’s ridiculous is that I knew all the stuff to do. I read the entrepreneur books, bought the courses from Welsh and Koe, consumed the appropriate podcasts, and took copious notes (too bad I’m not an investor in Moleskine or DesignWorks Ink).
But instead of getting out there and selling, talking about my product, well...
I kept tweaking the AI brain of the 2nd Act Launchpad.
I wrote DM scripts for when I would sell it.
I was busy as all hell. All that energy poured out and nothing but life lessons and moral victories to show for it. That kind of shit turns you into Uncle Rico from Napoleon Dynamite:
“If coach woulda put me in fourth quarter, we’d have been state champions. No doubt. No doubt in my mind.”
Filling my pool with the drain open.
It’s Not Your Fault (No, Seriously)
So what’s the deal?
Am I incompetent? A coward? A wimp who has subjugated himself to his inner bitch?
(I’m not going to answer that. Like I’ve said before, I’m working on my self-talk.)
The clinical literature will hand you a whole list of reasons: fear of failure, fear of success, the belief that you don’t deserve good things, and imposter syndrome. Every one of those is a symptom. The root is almost always childhood.
Which brings us to a sunny afternoon in upstate New York in 1996.
It was my last summer living in New York as a kid. GE was closing my dad’s division and he’d found something in Houston (where I was unsure about whether I’d take a bus or a horse to school). The gig was going to be an upgrade for our family, and we were leaving in August. My grandparents made the four-hour trip down from northern Boston to spend a week with us before we went.
My family was always on the fringe with that family. My grandparents weren’t strivers or climbers, very much ‘status quo’ people. And from what I can remember, they seemed to prefer status quo people.
My mom connecting with a striver (my dad) rubbed them the wrong way. The relationship went from bad to worse pretty much immediately, to the point where my grandparents didn’t even come to my parents’ wedding.
Fast forward to the middle of a weekday afternoon in ‘96, there was an adult conversation happening at our kitchen table while my 8-year-old sister and 6-year-old brother played close by.
I don’t know what was said. But the play-by-play afterwards is tattooed on my brain:
My grandfather pushing back from the table, saying, “I don’t have to take this shit,” and going upstairs to pack.
My mom at the front door, watching my grandfather load the bags, telling my grandmother, “You don’t have to do this.”
My grandmother’s response: “I have four other children.”
Me crying, holding onto the old man’s leg, begging him not to go.
The car backing out of the driveway and pulling up the street.
I was 11. If there was a lesson to be learned in the moment, I missed it completely. My reaction was akin to the little girl in Jurassic Park, watching the lawyer ditch the kids outside the T-rex paddock:
“They left us. They left us.”
Pouring Concrete
A month or so later, we lived in a new state where, turns out, I did not have to ride a horse to school. I adjusted by doing standard 11-year-old things. I don’t know what I was thinking about (I imagine a mix of baseball, video games, and babysitter cleavage), but it wasn’t the day my grandparents left.
Three or four months later, I biked home from school, the big 6th-grader who was responsible enough to commute solo.
When I opened the side door into the kitchen (the new house had two public-facing doors, movin’ on up), I immediately knew something was wrong.
My mom was sobbing at the table. My sister and brother were comforting her. I asked what happened, assuming someone had died.
My sister looked over at the phone on the counter. “Play the machine.”
Someone had died. My mom, it turns out.
I heard the voice of my aunt (who I’d thought was cool up until that very moment):
“Judi, now that you’re gone, don’t ever come back. As far as we’re all concerned, you’re dead and buried.”
My aunt. Mom’s sister.
For the first time in my life, I thought about seriously hurting someone. With a baseball bat. A shovel. Something that’d do real damage.
I was fucking furious.
But what could I do? I was 11. I followed my sibs’ lead and hugged Mom, too.
Dad came home a little later, and I’m sure we talked about it as a family. I don’t remember that. We definitely spoke about it again, but I don’t remember that, either.
I couldn’t see it then, but my brain wrote a new rule: some new ghost program running in the background. I didn’t even register its existence until I forced myself to unpack my most recent launch flop.
My dad’s division got shut down, he went and found something better for his kids, and his wife’s family buried her for it.
The rule I learned that year?
Moving up means people leave.
Keeping your head down means you stay safe and loved.
That went into the concrete. It hardened.
And I built my life on top of it.
I didn’t see my grandparents again until I was 18. When I was 22, I put them in my rear-view mirror. Beyond a brief, unwelcome visit from my grandmother in the toughest season of my life, I never saw either one of them again.
Nothing’s special about my story, because none of us get out of childhood without a fucked up rule or two being written.
Somewhere along the way, you learned that being big cost you something you couldn’t afford to lose.
So you learned to stay small.
Discipline Won’t Save You
Before it was self-sabotage, it was armor.
The rule kept you safe. That’s why it’s so damn hard to let go of.
You probably don’t even know you’re wearing it. I didn’t. Over the next 30 years, I maybe thought about the driveway and the answering machine half-a-dozen times.
It only came back up because I had kids, to be honest. Parents will tell you, watching little humans go through childhood makes yours more accessible. Things tend to pop up (sometimes, it’s a jump scare).
And when it surfaced, it wasn’t dramatic. It was more like, “Oh. Yeah, I guess that would be traumatic for a young kid.”
You can’t overpower it with discipline, either. I tried. But the same discipline habits that helped me achieve other things in my life (getting in shape, cold plunging, riding a 715-day streak learning Spanish) never had an impact on my playing small.
When I’d self-sabotage, my negative self-talk would go through the roof. I’d look in the mirror and rip myself apart: You little bitch. What’s your problem, pussy?
That voice felt normal to me. The anger had ‘always’ been there.
I can bully myself into my cold plunge, but for this, it was the wrong motivation. The 41-year-old didn’t need more discipline. The 11-year-old needed to be told he was safe.
I needed to take that little boy by the hand and tell him, “It’s ok, little dude. You’re enough. You don’t need to keep your head down to keep us safe.”
I needed to let 11-year-old Mike know his watch has ended. It’s not his problem anymore.
The 41-year-old father will take it from here.
And by the way, kiddo: he carries a big-ass bat.
Just in case.
“Man Your Own Jackhammer”
The concrete set. It’s not your fault.
It is, however, your responsibility.
This exercise is how you drill deep enough to figure out what’s holding you back, and take a few steps in the direction of unfucking yourself.
Knowing the rule exists isn’t enough. We know a lot of things we should be doing and aren’t. You need to go find yours, in writing, and relieve the exhausted kid who wrote it.
Let these questions take as long as they take. The stuff that comes up first is likely to be surface-level. Jackhammers aren’t built for surface-level.
Write long-hand if you can, computer if you have to. I prefer paper because burning is more satisfying than deleting.
Question 1: What’s the specific move I keep not making? Keyword: specific. “I’m not starting my business” is vague. “I’m still snacking on the couch watching Netflix and I’m not losing weight” is specific.
Question 2: What rule would need to be true for this behavior to make sense? Somewhere in you, there is a rational child who is thinking this behavior is protecting you. What’s going through their little skull?
Question 3: What action would I take if the rule didn’t exist? The advice you’d give your best friend. The thing the audience would be screaming at the screen.
Question 4: What new rule would have to exist for me to take that action? You lived a big chunk of your life running a shitty, autopilot rule. Write the new one. Be the architect of the life you want instead of the victim enduring the life you were handed.
I didn’t have these answers for my coach in the moment.
But by the time I was done journaling, I figured out what was holding me back.
For the last couple of months, I’ve been telling that 11-year-old that everything is OK.
I started sending the DMs for my program. Some got replies. Others didn’t.
I don’t really care one way or the other.
Turns out, the fear was total bullshit. So was the self-sabotage.
I finally put down my armor because I don’t need it anymore.
The kid still reaches for it, but I think he’s starting to trust me when I gently lower his arm.
Don’t worry, little dude. I’ve got this.