As a kid, I had lots of dreams and ideas. Regardless of how bad or outlandish the idea, my mom always listened and encouraged me. She let me know I could do or be whatever I wanted if I set my mind to it and worked hard. Her encouragement during my formative years gave me a solid foundation and the confidence to pursue entrepreneurship (and all my other ideas, good and bad) over the years.
Happy Mother’s Day, Mom! I appreciate your love and support!
When All Is Said and Done, What Will You Regret?
I listened to an old interview of Jeff Bezos explaining why he decided to leave his stable job to start Amazon. Not just any job—a high-paying job at an investment banking firm on Wall Street. It was a tough decision that he ultimately made using what he described as a regret-minimization framework.
He projected himself into the future to age 80. He wanted to minimize the number of regrets he would have as he looked back on his life. An important part of his thought process was identifying the things he’d regret not trying, even if he failed. Starting Amazon was one of them—even if it meant giving up his stable lifestyle.
I’m a huge fan of starting with the end in mind and working backward. I haven’t used a regret-minimization framework, but I’ve thought about what I want people to remember me for when I’m long gone and used that as a compass when making decisions.
For those fortunate enough to be able to consider only regret, I think it could be a good way to evaluate big decisions.
Do I Have a Good Reason for Doing It?
When I was younger, I made a series of decisions rooted in groupthink. Everyone else was doing it—whatever “it” was at the time—so I figured I should too. Some of those decisions proved to be painful. Upon reflection, I realized I was following the crowd instead of thinking for myself.
These days I’m very aware of this. If I find myself thinking about doing what everyone else is doing, I’ll pause and ask myself why I want to do it. If I can’t identify a reason that’s specific to my situation, I go the other way. This is difficult and sometimes isolating, but it’s served me well over the years.
I feel we’re in a period of escalating groupthink in a variety of areas. The people who think for themselves will be uncomfortable in the short to medium term but will ultimately be proven correct.
Entrepreneurs Don’t Retire – They Refocus Their Fire
I’m a big fan of YouTube. It’s an amazing educational tool for users and a powerful distribution method for smaller content creators.
I watched an episode of The Pivot where a professional athlete announced his retirement from the NFL. It was evident that he isn’t planning on slowing down anytime soon. He’s in his early thirties and has been building a variety of businesses in anticipation of his retirement. He’s planning now to build these businesses at full throttle and also spend more time with his family. He’s not thinking about winding down. The participants pointed this out and agreed that retirement isn’t the right word for his announcement. They decided to describe his announcement as a “career change” instead. This really stuck with me.
I have a few entrepreneurial friends who’ve been blessed to achieve financial freedom. They can do what they want, when they want. They joke that they’re retired, but that couldn’t be further from the truth. They’ve all started putting their time and energy into their next thing, whatever it is. They’re all doing something. None of them are idle.
Most entrepreneurs have a fire that burns inside them that can’t be extinguished. They focus that fire on what matters, and it’s often building companies. They aren’t the kind to retire and do nothing. Instead, they refocus their fire and change careers.
I spent Q4 of 2021 thinking about what I want to do differently. Historically I’ve set goals, but I always thought something was missing. You can do everything that’s in your control and still not achieve a goal. I never liked that, and I decided to focus on habits and systems in 2022. I read Atomic Habits and crystallized the habits I want to have that align with my identity.
I began implementing my new habits at the beginning of the new year. It was harder than I expected. I struggled to be consistent with all my new habits, and as I did, I realized that I need to simplify and focus on the one habit that will up the likelihood of my sticking to all my habits. So I did—and it’s been a game changer.
I’m now measuring one action every day. I have data for only a few weeks, but it’s clear. When I do this one thing that I want to be a habit, my days are much more productive and balanced and I get the outcomes I want. When I don’t, I’m far less productive, I’m reactive, and I don’t get the outcomes I want. This habit has such a big impact on my day that I consider it a foundational habit.
Figuring this out has changed my thinking about habits. Maintaining them felt like tons of work, and I wasn’t sure I could do it. Amazingly, it now feels like an easy life that I can maintain. I’m still doing the same things—it’s just how I think about them and what I focus on that changed. Glad I figured this out!
My parents raised me with a certain set of values and morals, which I stuck to. As an early founder, I always assumed others operated similarly. But as my entrepreneurial journey progressed, I learned that wasn’t always the case.
A few of our customers took advantage of us. We sold automotive parts to consumers and had customer-friendly policies around returns and other service situations. They were great for most of our customers, but they also attracted fraudsters. We got hit with a rash of fraudulent transactions in the early days. Caught off guard, we didn’t know what to do to fight them. In the end, they cost us a significant amount of money I didn’t have. We learned we had to be more aware of what was going on with our orders. We implemented systems and processes to identify suspicious orders. I also had our team take an aggressive stance vis-à-vis orders that we deemed fraudulent after they were shipped. Fraudulent transactions dropped sharply, to the point we rarely saw them. Fraudsters knew we’d fight back and weren’t an easy target.
And a supplier walked all over us. This company was orders of magnitude larger than my company and our main supplier at the time. Knowing this, they used their scale to push us around. They’d change our payment terms on the fly, which affected our cash flow. They’d change our pricing on a whim, which made us less competitive and reduced our revenue. They’d limit our ability to sell certain products, too. All these moves were made to optimize the relationship for the supplier at my company’s expense. Once I realized this company was looking out for itself—and only itself—I changed our strategy. I instructed our team to take an aggressive stance with them. We pushed back strongly on one-sided changes and even cut them off as a supplier. That company began to reverse their decisions and operate with more of a partnership mentality. They learned we weren’t a customer they could push around.
From these situations and others, I learned how important it is for a founder to be situationally aware. You can’t count on everyone to be honest and fair all the time. Your business, your people, and your money are on the line. You have to pay attention. You must understand when you’re in a situation where bad actors could prey on you or parties you’re involved with could do harm if given the opportunity. And you have to figure out how to protect yourself.
New Year = Opportunity for New Routines
Today is my first workday of the new year. I spent part of the day talking with founders about their plans for 2022 and what they plan to do differently. I told them that I view the beginning of a new year as an opportunity to set the tone for the rest of it.
Most of the year, I have a routine. I go from week to week doing the same things (good or bad). The Christmas and New Year’s Day holidays give me a significant break in the routine. When the holidays end, it takes a bit of energy to get back into a groove—it doesn’t just happen like it does after a weekend.
This window of time when I try to get back into the groove is an opportunity. I like to think about what worked and didn’t work and the new routines I want to establish. I then spend time establishing a new groove instead of just jumping back into the old one. Once I’ve entrenched my new routine in the first few weeks of January, I’m likely to maintain it for the rest of the year.
Looking forward to establishing my new routine for 2022 over the next few weeks.
Today is the last day of 2021. I’ve spent some time thinking about the last 364 days and how they compared to 2020. This year was busy and fast-paced. It went by in the blink of an eye (unlike 2020, which seemed to drag on forever). Lots of new norms were established, and I learned how to thrive in an environment of macro uncertainty.
If I had to sum it up, 2021 was a year of growth for me.
I’m glad to have made it through another year, and I can’t wait to see what 2022 has in store.
Personal Operating System
I listened today to a great interview of a successful entrepreneur and investor. One part of it especially stood out. He was asked how he manages to relax even though he’s constantly engaged in high-output activities, and his answer was enlightening:
- Simplify life – He doesn’t want more things in his life that he must think about or do. He minimizes the number of daily decisions he has to make and the things he does regularly. He constantly downsizes to further simplify his life.
- Avoid mental chaos – He could do lots of things, but juggling too many things creates mental chaos and stress. When he’s stressed, his energy changes, he’s not in a good place, and he’s not effective in his work. To avoid this, his default response is no.
- Hyper focus – He says yes to something only when he anticipates massive output for a decent amount of effort. He will hyper focus on that project, blocking out time on his schedule to do so. The rest of his time is unscheduled and used for relational activities and learning.
- Optimize his “personal operating system” – He knows what he can handle and how he operates best. He doesn’t want to overload his personal OS by taking on too much. Instead, he optimizes for a few things that have the potential for a big impact.
This approach is unique. It’s counter to what I’ve heard from other successful people. I really like how he is so self-aware that he’s able to optimize his approach to what works best for him while ignoring how other people manage their work and lives.
Embracing My Holiday State of Mind
This past week was a much-needed holiday. After not celebrating Thanksgiving or Christmas in 2020, I’ve been looking forward to this holiday season. I went into Thanksgiving excited and also focused on being more intentional. I was looking forward to spending time with others, and I wanted that time to be high quality—I wanted to be present and engaged. I tend to not be as engaged if I’m in work mode, so I decided to not look at anything work related through Saturday. Overall, I think the mission was accomplished. I enjoyed the holidays, was able to unplug a bit, and was mentally as well as physically present with people I care about.
Today I started to prepare for the coming week and noticed I wasn’t being very productive. It was taking me longer to get things done and I wasn’t as focused as usual. I guess I was having a bit of an off day during my holiday. Today is Sunday, and my brain refuses to leave holiday mode even though I wanted to put it in work mode. Instead of fighting it, I recognized what was happening and leaned into it. It’s been two years since I had Thanksgiving, and it’s clearly something I’ve missed. I decided to put the work away and enjoy the last day of my Thanksgiving holiday!