Humility & The Leaky Bucket

This year I had to take a large dose of humble pie.

January 01, 2022

I’ve done yearly reviews in the past, and I’ve made predictions about the future year. Both of which were rife with survivorship bias and were largely useless. Simply opportunities to drive clicks and boost my self esteem.

This year I wanted to talk about the last year from a different perspective: one of productivity, longevity, and my intentions in regards to the future of me and my family.

In short - I (Closet Tools) make(s) less money now than I did January 1st 2021. My ego has taken a slight hit, but I’m reminded that it’s all because it falls in line with what I truly value and what matters to me.

And no, I’m not trying to brush over the fact that this isn’t a good thing necessarily for the business. It’s not. I’m not trying to make it seem like everything is sunshine and roses.

However, my life is better now than it was a year ago - in regards to how I spend my time, the relationship I have with my wife and kids, how I build wealth, and how I think about preserving my future.

This year I had to take a large dose of humble pie.

A year ago I was a big shot. Untouchable. Everything was up and to the right. I could do no wrong. Sure, I didn’t have the best marriage. Sure, I didn’t eat well and took pain killers at least once a week to mediate headaches. Sure, I didn’t save properly for taxes and overspent.

None of that mattered - as long as the business kept growing my problems could be “solved” with more money.

Boy was I wrong.

When the business stops growing, and starts shrinking, you’re forced to look at how things are right now. You can’t simply project out into the future and plan bigger and better things, you have to take stock of what you have and how you can ration it in case of a catastrophic event. You don’t know what the future holds because you thought it was going to go up, and it went down.

MRR In 2021

There are a few reasons it stopped growing so much - I relaxed on marketing, a few competitors popped up with influencer backing, and my documentation didn’t properly keep pace with the features I have been shipping out. I have been increasing the value provided to customers without charging more. The onboarding flow got more confusing and less simple. The more I do that, the more I pay out of pocket per customer.

But that’s not interesting to me. I know all of that, and it’s whatever. What matters to me is that I shifted my mindset this year. I’m no longer the “all star”, the guy who has all the answers. It turned out that I needed to strike a balance or everything that mattered to me was going to crumble.

This year I worked from the ground up to restore my marriage, change how I spent my time, truly have a plan for finances, and think longer term about what I’m actually going to do with my life.

To me, that’s so much more important than having a thriving business that only goes up and to the right. What does that matter if life at home sucks? Or if I’m not healthy enough to enjoy spending time with my kids? Or if I can’t even control where my money is going?

All of these pitfalls in my life took time to restore. Like usual, I don’t have all of the answers. I’m not perfect. But what I can do is tell you what I did to get control over my life and address some of these issues head on.

A winning marriage

I now regard my marriage over almost everything else in my life. It’s the most important thing. Without a healthy marriage, my kids are not secure and will reject my instruction. Without a healthy marriage, there are constant distractions that keep me from doing my best work (and her from doing her best work). Without healthy communication in a marriage, life is confusing and every day is different. It’s hard to make progress when you’re having the same discussions every day.

I did a few things to remediate these aspects:

  1. We have a babysitter come watch the kids weekly while we go out on a date (every Thursday). In the past we never really went out, and especially once we had multiple kids.
  2. I write a note to my wife every weekday morning outlining the day, updating her on finances, expressing some of my feelings, and thinking ahead about various projects/plans/events.
  3. We established a daily routine that’s the same every single day (weekdays and weekends), so we have a routine that allows us to have quality time spent together, as well as quality time spent apart doing the work that we want to get done. We both take various shifts with the kids. Then, we come together and clean/cook/play as a family.
  4. I added several of points of accountability to ensure to my wife that I am doing the things I say I am going to do, and that I am being trustworthy and honest. I’m now much more cautious to promise, and quick to double down on doing the things I say I am going to do.

A year ago things were so confusing. Life should have been great, but it wasn’t. There were a lot of issues that needed to be addressed, and they weren’t going to address themselves.

I can safely say these changes are implemented in a way that’s sustainable and built to grow our marriage for the long-term. I’m excited about the future of our family, and it makes me feel at peace about moving forward in life through good times and bad.

Financial awakening

I’ve never been a spender, but I’ve never been good with money. I’m generous to a fault, and I get stressed if the numbers don’t add up to what I expected. I constantly “took ownership” of finances, and then neglected them more and more over time.

My thought process was that as long as I continued to make more money I didn’t really need to be good with money. Everything would work out, and life would be grand. Boy, did I have a rude awakening.

You see, as long as you continue to make more money it’s easy to not save for taxes all year, and then just cram in saving at the end of the year. Just a couple of months of pain. But, when the business starts to shrink - all of a sudden the taxes of the past begin to overtake what you’re making now. All of a sudden I was needing to save 70%+ of my income simply to pay taxes for the past year (not even including paying taxes for this year).

It was a mess, and I’m still cleaning it up. However, I have a plan and I am sticking to it. It should all work out fine, and I have made a lot of changes about how I handle money and how I pay attention to our finances.

Now, my finances are mostly automated. I take a percentage out of every paycheck for taxes, for tithe, for bills, for saving, for investing, and for groceries/expenses. Then, the rest is up safely for grabs for my wife or I to spend.

This works well because whatever is in the joint checking account is available to spend - knowing everything else is properly accounted for. My wife doesn’t have to ask me every time she wants to buy something. I don’t have to tell her what’s available and not available. It just works.

This is what I should have been doing all along - hindsight is 20/20. But I was lazy, and truly thought as long as I just made more money things would be fine (which was technically true, but very stupid of me to not account for things taking a downturn).

My time is accounted for

Having a stable routine is something new for me (at least, in my adult life). In the past things were always slightly different each day. I would wake up at different times, go to bed at different times, work at different times, eat at different times, etc.

That has all changed now, and every day is exactly the same. The number one benefit of this is that I don’t have to talk extensively to my wife about the plan for the day. It never changes. The specifics might change (like, what I am working on, or what we are making for dinner), but the schedule never changes. This has given me so much more energy to be able to get more done in a day than ever before.

Back then I had no idea how my time was being spent. I didn’t know how much I was working, or how much time I was spending with my kids, or how much time I was spending with my wife. I was just going with the flow.

Now, I am directing the flow. I know exactly how much time I spend doing everything, and it’s easy to pinpoint exactly why I feel the way I do (if something is off). When I don’t stick to the schedule things start to go off the rails and not everything gets done that needs to get done.

With this shift I have had to make some adjustments that I am still working on - like being productive during specific times of the day, and not just when I feel productive.

It’s not easy to write, code, design, etc. when you’re not feeling inspired. It’s a chore to push through the few hours you have in a day to work to get necessary work done. It’s not like a traditional 9-5 job where you have a couple of hours of real work to do in a day and you can pace it out for whenever works best for you. I need to be on my game and productive as soon as I sit down to work, otherwise I get nothing done.

So even though having a strict schedule is way better than not having one, I’m still working on maximizing productivity in regards to my work. It takes a lot of effort to eliminate all distractions and sit down and focus on one task for an hour or so, and then move on to the next task.


In 2022 I have four things to accomplish (professionally):

  1. Finishing
  2. Finishing a major feature with Closet Tools, and improving documentation/onboarding.
  3. Shipping a new SaaS product.
  4. Learning and exploring trading microcap cryptocurrencies.

I would like to have the rough (like, really rough) draft of Rank To Sell done by the end of February. Then, a few more months for testing and iteration before formally publishing and finalizing. I’ll be Tweeting throughout as I write the book to continue gaining attention.

Closet Tools is in a rough spot - it’s way more powerful now than it was a year ago, but it’s also a lot more complicated and not obvious how to get the most value out of it. I have one more major automation piece to complete, as well as several minor features to complete in the next couple of months, and then I will switch to a more marketing/documentation/customer success role while I ship a new product.

The new product is “lips sealed”. I’m not revealing anything, and I won’t tell anyone about it except for the specific people I invite. I will take time to get feedback and iterate on the product before releasing it publicly and allowing anyone access. I hope to start this towards the end of Q1 and go harder on it in Q2.

I am still interested in automated trading and investing in cryptocurrencies. I still have (though, the original intention was slightly different), but I will shift focus to earning multiples in early stage tokens. I have no plan for this right now, but it’s something I am going to be focusing on.

That’s really it. Everything else is largely the same - lots of time spent with my wife and kids, lots of time spent sleeping, eating healthy, and playing/exercising, and lots of time reading my Bible and books that interest me.

2022 is probably going to be a pivot year for me - not the best year of my life, but a foundational year that sets up the next 5-10 years of my life (whether it’s my life as an author, or a founder, or both).

I hope you enjoyed this real look at what happened in 2021 for me, and I hope it inspires you to take action on making your life better in every way (not just in business).