Procrastination and Shame

Reflections from the Past 2 Weeks

In my last email, I mentioned that I thought I had to make a difficult decision.

Honestly, I already knew what decision I had to make. I just needed to do it. Right after I sent that out, I messaged my cofounder and shut down DeFiNet.

I’ve been working on what I want to do next. I’ve started reaching out to people and talking about potential opportunities.

I also started a new book club. Our book is “The Gifts of Imperfection” by Brene Brown. We had our first meeting this past week. The first part started with identifying things that hold us back from joy and happiness: fear, shame, and resistance to vulnerability.

This really hit me hard. I’ve been trying really hard to ignore all the signs that DeFiNet wasn’t working. But when I really knew, I knew. But I wanted to know why I didn’t let myself see it sooner.

How does it feel to fail?

I had to start thinking about how I felt. I made a bit of a big deal out of launching a startup. I started pursuing my vision with reckless abandon. That’s the key to success right?

No, it’s really not. That can sometimes help, but there are better ways. One thing I can say: I tried a lot of different things. And I failed a lot of different things. All of the small failures were learning experiences. I thought these experiences would keep me from experiencing total failure: shutting down DeFiNet. I could deal with the small failures. I knew they were par for the course. They hurt less and less over time. But what about ultimate failure? That hurts a lot.

I didn’t feel like I even got a fair shot. It felt like every little thing went against me. I saw so many possible wins fly past as losses. It sucks when you do some things right and still lose. I’ll admit that I didn’t do everything right. But damn it, I did a few things well. I had to reflect on where I could do better.

As I’ve done a post mortem, I’ve gotten a much better idea of why I failed. First and foremost, I had the wrong cofounder. That’s a relationship I jumped into and it wasn’t right. We had two different visions for the future and two completely different communication styles.

And a lot of that is on me. As I’ve started to understand how the Autism part of my brain handles things, I’ve realized that for a relationship as close as a cofounder, I need a very specific type of person. I don’t know exactly who that is yet. But I have a much better idea of the type of person I need. And I’ve learned that I don’t need a cofounder.

I had some ideas early on. Before I met my cofounder. I had a vision. But when I partnered up with my cofounder, I started compromising on my vision. I was trying to achieve his vision and mine. I didn’t know how difficult it is when cofounders don’t share the same vision. It’s pretty much impossible.

I did the same when I would talk with investors. Too often, I adapted my idea to what I thought they wanted to hear. I started off with one vision and modified it to impress investors.

But I’ve realized that I don’t need to do that. I’ve got to do two things. I’ve got to start building. And I’ve got to learn how to communicate my vision to the right investors. That’s something I’ve learned a bit about too. It’s really important to find the right investors. I talked to quite a few investors over the past 6 months. Now I’ve gotten a much better idea of what I need to show them. I’ve also realized that I may not need them.

I just took the first half of a Financial Fluency course. I was supposed to take the whole thing, but unfortunately, an internet issue postponed the second half. I’m going to have a ton I write about from this course, but one thing stood out to me above all else. As a business owner, you are the primary investor in your company.

That hit me like a sack of bricks. From the beginning, I assumed that I needed an investor. I needed someone who knew the numbers side. I didn’t have a background in accounting or finance. I needed someone who took care of that part of it.

Didn’t I?

According to Sir Steven Wilkinson, the answer is no. Anybody can understand finance with the right mental model. I’m starting to understand what a business truly is. I thought the goal of a business was to manage money for a group of people. And that’s kind of right. But it misses out on something more basic. A business, first and foremost, exists to solve one or more problems. An entrepreneur is someone who allocates available resources to solve a problem. If you don’t know what resources you have, how do you allocate them?


I think procrastination and shame are often linked. If you are worrying about what others will think, that delays what you produce. And when you end up missing deadlines and things like that, shame can really set in. I’m going to be honest with you. I had this email mostly written by Sunday, but I lost track of where I was and didn’t get back to it. I thought about it a few times and definitely felt pangs of shame, realizing that I missed my (self-imposed) publication schedule.

While I’ve been trying to figure out what’s next, I’ve started thinking about what I’m good at. And I realized something.

I realized that my biggest coping mechanism is my most valuable skill.

Let me explain.

One thing I’ve always loved is automation. I’ve always looked to automate various pieces of my life. At work, this usually helped me by establishing guardrails for myself. Usually, I’d forget to do something because ADHD, and so I would automate it.

And the last few years at my job, most of my time was spent figuring out how to automate various processes. When I wasn’t automating reports, I was automating our build processes or our data flows. All automation, all the time.

I’ve discovered that it helps prevent procrastination. If I have automated systems around me that can alert me when my intervention is needed, I become much more effective.

Turns out, there are a lot of people who don’t know how to automate everything. I’ve been working the last few days to launch a new consulting practice around automating business processes for small-and-medium businesses (SMB).

I’m also examining my own processes and automating what I can. I’m still figuring out exactly how I want to automate this newsletter to help things along, but I’ll figure something out. But instead of feeling shame, I’m going to perform self-love, not hold it against myself, and make sure I still get it published.

Until next time.

Think about where you could automate your life to save time. Next time, I’ll describe a framework I use when I’m trying to figure out what to automate.

Here’s something I wrote about automation.

Maybe it will help.