During my late teens, each time I got caught shoplifting and had to deal with the consequences, my mind would dwell on what I could have done differently. I went over and over different actions I could have taken to avoid the arrest.

This helped me get better at shoplifting. Each arrest or near-arrest made me refine my techniques. I learned to shoplift more valuable items and at lower risk.

I started out stealing candy bars and cassette tapes. Several months later I was stealing video games and small electronics like telephone-answering machines – remember those? Then I progressed to larger items like TVs, cutlery sets, and appliances worth hundreds of dollars.

I could walk into a retail store and walk out with $300 to $700 worth of merchandise. And these weren’t small items. My main limit was how much I could physically carry in my arms.

It may seem hard to believe that someone could walk into a department store and steal a 27″ television – the big, heavy, and boxy kind before the days of flat panel displays. I could barely carry it myself.

I could do this kind of stealing without my heart skipping a beat. It became somewhat routine after a while… till I finally got arrested for felony grand theft and almost went to prison for it. Then I finally realized it was time to straighten myself out.

Before I’d done any shoplifting, I would have thought it impossible to do these bigger thefts at all. You might be wondering that as well. Someone can just walk into a department store, steal a bunch of large items, and walk out with them? Yes, during store hours in plain daylight. I personally did that dozens of times about 30 years ago.

What about anti-theft sensors? Security cameras? Plain clothes security guards?

There are counter-measures for all of those, and most of the ones that worked 30 years ago would still work today.

Every mistake I made back then led me to develop better counter-measures. Setting off a blaring sensor device while trying to steal a Sega Genesis game cartridge encouraged me to learn how to defeat anti-theft sensors. Getting caught by a guard who saw me made me more aware of that risk, and I adapted my methods. Getting caught another time due to being seen on a security camera led to a reevaluation of how to avoid that problem, which led to a whole new method that was exceedingly hard for a camera to catch.

Consequently, although I did get caught and arrested a bunch of times, I never got caught for the same type of mistake twice.

I was also caught more than I was arrested. By developing more sophisticated techniques, I was able to weasel my way out of a capture to avoid an arrest. Any point in the chain could have a weakness, and you just need to turn one weak link to your advantage to break the chain of events that lead to arrest. You can even break the chain after getting arrested; a couple of times I was arrested but not convicted.

I recall that a two-stage shoplifting technique I had developed served me well. I specifically designed it to reduce my risk. In some situations, I could divide the act of shoplifting into one step of preparing to steal and a second step of actually stealing, and those steps could even be done days apart. Once I was caught during the first stage, which didn’t include the actual theft. The guards were certain that I’d stolen something when they grabbed me leaving the store and pulled me into the security office. But they were left confused, embarrassed, and angry when they searched me and came up empty handed because I had no merchandise on me. They knew I’d done something very much akin to shoplifting, but they had no proof. They knew I was lying about it too, and they absolutely didn’t buy my explanations, nor did they take kindly to my feigned anger at them for their “mistake.” But it still worked. Just to be extra safe though, I never went back to that store again. Today that whole chain of stores is out of business.

When I first started on that path, I couldn’t have perceived where I’d end up a year to 18 months later. It was really just a series of small progressions and refinements, motivated by the pain of mistakes and the thrill of doing illegal stuff. Each time I grasped for slightly better methods that reduced risk and increased gains. I also pursued it because it was fun, at least for my teenage brain at the time.

When I think about the progression of little refinements, no single refinement seems like such a big deal. I was really just reacting and adapting to events.

But when I consider how far things went over the course of 12-18 months, I wouldn’t have believed those distant outcomes to be possible when I first started shoplifting. I couldn’t fathom ever reaching that point. It would have seemed like way too much of a stretch and way too scary. No way would I ever take it that far.

And yet I somehow did, one little step at a time, with the biggest improvements happening in response to getting caught.

Here are some key lessons I learned from this progression, which doesn’t have to be applied in an illegal or self-destructive way. You can apply this a lot more positively and productively to your life.

First, this all started with following the fun. There was an inner motivation to stretch and tackle an interesting challenge that seemed fun, even if it was also illegal. Later in life I learned to use this heartset for other worthwhile personal growth pursuits. I looked around for something that seemed fun and emotionally engaging.

Second, anything fun eventually becomes boring if you keep doing it in the same way. So if you follow the fun, that will encourage you to keep escalating in some manner. The path of fun is also the path of escalation. Such paths can be dangerous or beneficial – or both.

Look for a path that eventually escalates into territory that seems impossible for you but also impressive when you think about other people taking it that far. Can you see beyond the edge of possibility space and into the impossibility space if you look further down the road? Imagine where you might end up if you just keep escalating again and again.

Does the impossibility space scare you? If it doesn’t scare you, it’s probably not worth pursuing.

Consider that fear points to future fun that you’re currently incapable of accessing and enjoying. A good progression eventually looks scary. If you look far enough ahead, you’ll see “impossible” actions that you’re convinced you’ll never take.

This points to needing a healthy relationship with fear. It’s important to see fear as an invitation, not as a barrier. Fear means “not yet but eventually.” Fear doesn’t mean “never.” This is a hard thing to wrap our minds around, but we can see the truth of it with our hearts a lot sooner. Your heart will say, “Yup, you could take it that far,” while your mind is still freaking out at the very notion.

See the logic in how to make the impossible eventually possible for you. Just keep following the fun. Keep escalating gradually so it stays fun and doesn’t becoming boring. When a risk becomes a non-risk, find a new risk to replace it. Focus on the risks that are in your fun zone.

You’ll fail and stumble sometimes. When you do, modify your approach to remedy that point of failure, so you’re less likely to fail that way again. Don’t worry about all possible points of failure. Accept that sometimes you’re going to fail, and you’ll have a new learning experience each time.

In the past 30 years since those shoplifting experiences, I’ve gone through much healthier and saner progressions in different areas of life. A lot of what I experience as normal today would have been squarely placed in my impossibility space 30 years ago. My work, my skills, my marriage, my home, my lifestyle, my friends – all would have been deemed impossible for me by my former self. None of this seemed accessible.

This also taught me that if I want to set meaningful long-term goals, it’s good to aim for something that extends into my current impossibility space. If I only reach for what’s possible, I’m probably not aligned with the fun zone. I’m being too safe and not taking enough risk.

It’s possible to check off a lot of smaller goals as part of the progression towards a seemingly impossible one, and this can be a lot more fun and motivating than aiming for the seemingly easier goals directly.

After I lost interest in stealing and getting arrested, I still kept following the fun, but I opted to stick with legal options. Some were still in the direction of that cat-and-mouse game with corporations, not that dissimilar from shoplifting in the emotions I experienced. Learning to count cards at blackjack and playing in the Vegas casinos when I was 21 was one example. It was totally legal, but there was still the chance of getting caught for it. It felt sneaky. There were skills to be learned. And there were ways to escalate the experience to keep it fun and engaging.

By continually following the fun, escalating it, adapting to setbacks, and progressing to something new when the whole chain became boring, uninteresting, or impractical, I eventually started moving in the direction of more positive and socially constructive progressions like writing, speaking, creating courses, and delivering workshops.

I also shifted my character a lot. Shoplifting would be out of character for me now, but I still love experiences that involve a similar emotional journey with risks to embrace and fears to face. This includes learning to make a good living without a job, overcoming fear of public speaking, going vegan, and doing lots of interesting challenges like the daily blogging challenge for this year (only two weeks left to go).

What I find especially fascinating is that even though I started out following the fun by committing crimes, this same heartset eventually turned my life towards meaningful goals, service to others, and a sense of purpose, including the development of a lot more emotional intelligence that includes caring and compassion. While I was doing the shoplifting, there’s no way I’d have considered any of those eventual gains to be within my possibility space. I wouldn’t have wanted them or cared about them either. In fact, I’d have actively shunned them.

Fun and risk seem like reckless or childish frames, right? But imagine where they might lead you over time if you keep dancing with them as I’ve suggested. Eventually a life of non-purpose gets boring. Living in the shell of a weak character gets boring. Being too undisciplined gets boring. Not caring about people gets boring. Watching life pass you by without fully engaging with it gets boring.

It’s possible to have way more fun from contribution than from crime, mainly because of how human relationships are affected. So the approach that got me into those reckless behaviors also got me out of them and onto something better. I kept following the fun. I kept leaning into escalations that kept life interesting and engaging. I kept releasing whatever became boring. I kept aiming towards new impossibility spaces, only later to find myself living inside of them.

Can you trust fun?

Maybe you think about how ludicrous it would be if you just leaned into fun experiences, like playing video games all the time. I played video games a lot 30 year ago, as much as 18 hours in a row, and that was on Nintendo, Super NES, Sega Genesis, GameBoy, or one of those archaic systems with much less sophisticated one-player games, including the kind where you have to restart from level 1 if you run out of lives. Following that type of fun led me to play more games and to eventually become a professional game developer for 10 years, which was a memorable and rewarding part of my life (albeit frustrating till I figured out the business side).

I’ve had a pretty fun life overall, and it’s hard to feel regret even when I think about some of the wild and illegal stuff I did 30 years ago. I feel mostly gratitude and appreciation for those experiences and the lessons learned from them, especially since they shaped who I became.

My main regret is actually that I didn’t trust fun sooner. In many cases where I finally leaned into fun and risk, I wished I’d been able to trust it sooner and not worry so much about where it might lead. Even with the arrests and other setbacks, it’s still a lot better than being bored.

Fun is an invitation, not to do one thing forever, but to engage with life with your heart, not just with your head.

A huge risk that people tend to overlook is the risk of stagnation from being stuck in your head too much. The pursuit of fun, risk, and escalation are fantastic counter-measures.