Why We Often Sabotage Ourselves

Fifty-two months of Solopreneurship has surfaced one big realization:

This journey comes with a lot of hidden traps.

Traps of my own making. Subtle forms of self-sabotage that, at times, have hindered my ability to make progress.

I’ve fallen into these traps more times than I care to admit. But I’ve also reflected on these challenges, and I found some unique ways to overcome them.

So today I’m sharing some of the self-sabotage antics I’ve succumbed to. And I’ll tell you how I combat the sneaky problem of standing in my own way.

Self-Sabotage Tactic #1: The Mirage of 'Busyness’

Being busy every second of the day is worn as a badge of honor in the corporate world. The busier we make ourselves, the “harder working” we appear to our peers and the boss.

But in reality, busyness doesn’t equal productivity.

I should know. Early in my solopreneur journey I missed important family events and started down a path of burnout, only to realize that my busyness masked the fact that I didn’t have clear direction in my business.

My solution?

I started scheduling 'thinking time'. Dedicated periods for strategic planning, free from the clutter of busy-work tasks and social media. I find time everyday to just think.

Where am I going? Why? Where am I off base in my execution? Is this really the right direction for me? Or have I been influenced by something that doesn’t actually align with my goals?

It pays to think your way back into alignment.

Self-Sabotage Tactic #2: Chasing Perfection

Perfectionism has been an enemy of mine for a long time. And my perfectionism is a little bit weird — It’s not about making things perfectly flawless, but rather an endless tweaking of plans, delaying launches, waiting for that 'perfect moment’, which, of course, never comes.

A few years ago I leaned into a new mindset: progress over perfection.

I began using a 'good enough' metric: if a product, service, or newsletter met 80% of my vision, it was time to publish and move on.

This shift increased my output, and it actually helped me make stuff that was a lot better!

Take this newsletter, for example. This was an idea that was about 80% ready when I realized I was going to procrastinate my way out of starting. So I just launched. I forced myself out of my perfectionist comfort zone.

And the results have been a great learning experience. Over the last two years, this newsletter has gone through several subtle iterations to make it better over time.

So if you find yourself stuck in the fine tuning part of your project, try my “good enough” metric. If you’re 80% ready, consider putting your thing out there for the world to see.

You’ll get started — and you’ll get better for having done it.

Self-Sabotage Tactic #3: The Echo Chamber

When I started building my business, I had a handful of family members, peers, and followers who loved everything I did. Nothing but love and positive reinforcement.

Sounds nice, I know. But in reality, surrounding yourself with “yes people” is a form of self-sabotage. Because when everyone tells you you’re great, you don’t get the constructive feedback that is absolutely necessary to grow.

And this is on us. Naturally, most of us humans don’t create environments and relationships where people can give us honest feedback.

I joined a small Slack group of creator friends who are 100% honest and candid. Our whole job in the group is to help and support each other. And that means honesty is always the best policy. If I ask them to tear something apart, they do it, no-holds-barred.

This hasn't been comfortable, but it’s been incredibly transformative.

Connect with people who are willing (and able) to give you constructive feedback. Because  we can’t see our own blind spots. And fresh perspectives are helpful for any solo project.

Self-Sabotage Tactic #4: Shiny Object Syndrome

With varied interests, I get excited to explore different ideas creatively. So I can get distracted pretty easily if I’m not careful.

This became a problem when I found myself going hard on new projects, only to abandon them when something new caught my eye…over and over again. I had a blog back in 2020 that lasted a whole twelve issues, for example.

I can’t take credit for my diagnosing my own Shiny Object Syndrome. My wife was a good sounding board, and then I couldn’t unsee it.

While exploring different ideas can be good sometimes, the problem with shiny object syndrome is it will keep you from ever making real progress on one thing.

And I know this is a common challenge, especially for people building their own businesses. Whether it’s writing newsletters, recording podcasts, or posting on social media- it’s hard to stay on track and be consistent.

My answer to consistency is systems.

I have 90 minutes carved out every Monday to write this newsletter. Sometimes I use the whole 90 minutes, while other times, 30-45 will suffice. This is a rigid process I follow, and I refuse to remove this time block from my calendar.

Ninety-eight weeks later, this sacred block of time has allowed me to continue writing to you every Saturday.

I also systematized how I create content for both LinkedIn and Twitter that reaches nearly 200M eyeballs each year. Systems help you win.

Moving Beyond Self-Imposed Barriers

These realizations about myself were kind of uncomfortable to accept at first. But if you think about it, self-awareness is the first step on any path to improvement.

So now I just consider these simple truths about my personality to be aware of, and to actively work against.

As solopreneurs (and humans), our biggest challenges (and our greatest strengths) are often internal. We have a lot of power to do good for ourselves, or not.

Try to step back and take a good look at your own busyness and your projects.

Are you standing in the way of your own progress?

That’s all for this week. See you next Saturday.