Ben Sampson Headshot

Hey, I'm Ben!

I build, buy, and invest in businesses.

I've had 2 successful exits. Way more failures.

I write about building Freedom Companies to achieve what I call the three freedoms:

A life of financial freedom.
A life of time freedom.
A life of creative freedom.

I send one action packed email a week called a 1x1x1 where I write about businesses and people that I think are inspirational when it comes to creating freedom in their lives, or updates on the businesses we're building and buying.

This newsletter is the highlight of my week and I hope I can inspire and guide you to building your own freedom company.

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Hacking Boredom

I have a fear that may seem insignificant, but it is real and, at times, keeps me up at night. I have a fear of boredom. Fear that my career path will become boring, that my lifestyle will become boring, and that the decisions I make could potentially set me up for a life of… You guessed it, boredom. Now boring can be a broad state of being, but in this case, I refer to it as a life lacking of excitement.

This is a piece for everyone that has that same fear. A fear that you’ll end life quietly, in a planned fashion rather than skidding across the finish line burnt and bruised saying, “that was one hell of a ride.”

Ironically, boredom is sometimes required. More often than not, as life becomes more complex, boredom creeps in. The number of payments increases. The need to have a steady job becomes more apparent. Commute time only increases. You can find yourself in a state of repetition, looking at yourself asking, “Is this what I set out to do?” To live, to progress, or to support others, there are times in life where these elements are required, and they can feel “boring.” So how do you stay excited and engaged through these times? How do you hack boredom, even when it feels like you’re locked in your patterns? These are my cures.

Never stop learning

If you learn nothing new, how will you do anything new? There are two ways to accomplish this: learning via education or learning via active participation. A key theme that I have throughout this write up is momentum and progress = excitement. I currently fill this slot in my life with learning how to play piano. After learning piano, I’ll move on to boxing. After boxing … who knows. The key to doing this and feeling the progress is to set goals and stick to a timeline. The goal I set for piano was to play Dream of Flying by Brian Crain. I gave myself six months. To reach my goal, I decided to take piano lessons once a week, following that up with continuous practice of three hours per week. Tracking the progress feels good. A key thing to note is that I keep my personal and professional learning activities separate. I don’t count business classes, design/development courses, etc.

Do something that scares you — regularly

I actually ask myself the question: “Have you done something lately that scares the sh*t out of you?” Recently, the answer for me has been “No.” There was a time when I was much better at this, and this article has re-invigorated a need to scare myself more often. Pushing my limits and living at the edge of my understanding is, sometimes, when I feel most alive. The moments where you come out of a situation saying, “Wow. I did that” are gratifying. Examples for me consist of holding a five-minute conversation with a total stranger, trying food that looks terrifying, and participating in an activity or sport where death is a potential outcome (key is to keep your probabilities low here — let’s not get too crazy). Scaring yourself is the cold shower version of hacking boredom, and it’s a great way to get out of a slump.

Push the limit, and don’t stop pushing

Often times, our jobs can quickly become routine. If your job is becoming routine, then you’re not pushing hard enough to take it to the next level. Taking it to the next level can be grabbing a promotion, completing a project, or taking on more gratifying responsibilities. The goal should be to get to a position where you can have a significant impact on the company, or division of a company (taking size into account). Often times when you push for more with upper management, there can be push back. This is normal and a responsible course of action for upper management. Responses can consist of: “Let’s take some time to think about this and revisit.” “I’m glad you’re thinking about this, but I don’t think it’s the right time.” “We’re actually already doing this.” Typical behavior is to then wait and be patient. The time suck of boredom has begun, because the pushing for progress has halted until “a later date.”

Again, progress = excitement. It’s forward moving momentum that get’s the juices flowing, and the results deliver the gratification. Push back. Think of it as a negotiation. Responses can consist of: “How about we revisit this now?” “How about I do this to alleviate the other employee?” “What do I need to do to own this, and how can I expedite this decision?” “Let me do this. If you’re unsatisfied, I can revert.” If the passion and drive exist, your employer would be foolish not to give you the chance. Don’t stop pushing. Don’t remain idle.

Scheduled spontaneity

Saying you’re going to be spontaneous isn’t enough. Life will get in the way. If you don’t make it a required deliverable, you will rarely be spontaneous. Scheduled spontaneity may not seem very, well … spontaneous. However, the goal is to ensure the activity is spontaneous. For example, next Thursday, after work, let’s block for a spontaneous activity. We’re not going to plan what that activity will be until the moment we actually are ready to do the activity. Be random and do something completely different, even if it’s just for 30 minutes.

Step back, and look at your narrative

I think of my life as a movie. I think about the story line, the critical events, the building of a potential plot, and I think about what each scene is going to look like. My goal is to frame my life with those scenes. Sometimes I move away from my narrative, and I burry myself in a hole where no progress is made. If I don’t take a step back and look at the story line, I lose the momentum. I lose the excitement. This is just one figurative perspective, but the general idea is to take a step back and make sure your life is heading in the right direction. I try to separate myself from the world of tweets, emails, and phone calls for two weeks a year for my annual reset. This makes all the difference in the world. I highly doubt the movie you envision is boring. Follow your narrative. It will take you someplace exciting.

Boredom is scary. Hack it.