The Dabbler, the Obsessive, and the Hacker.

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In his book, Mastery: The Keys to Success and Long-Term Fulfillment, American writer  George Leonard describes the learning paths to mastery. He writes: We all aspire to mastery, but the path is always long and sometimes rocky, and it promises no quick and easy payoffs. So we look for other paths, each of which attracts a certain type of person.

The Dabbler, the Obsessive, and the Hacker

The Dabbler

The Dabbler approaches each new sport, career opportunity, or relationship with enormous enthusiasm. He or she loves the rituals involved in getting started, the spiffy equipment, the lingo, the shine of newness. When he makes his first spurt of progress in a new sport, for example, the Dabbler is overjoyed. He demonstrates his form to family, friends, and people he meets on the street. He can’t wait for the next lesson.

The falloff from his first peak comes as a shock. The plateau that follows is unacceptable if not incomprehensible. His enthusiasm quickly wanes. He starts missing lessons. His mind fills up with rationalizations. This really isn’t the right sport for him. It’s too competitive, non competitive, aggressive, nonaggressive, boring, dangerous, whatever. He tells everyone that it just doesn’t fulfill his unique needs. Starting another sport gives the Dabbler a chance to replay the scenario of starting up. Maybe he’ll make it to the second plateau this time, maybe not. Then it’s on to something else.

 The Dabbler might think of himself as an adventurer, a connoisseur of novelty, but he’s probably closer to being what Carl Jung calls the puer aeternus, the eternal kid. Though partners change, he or she stays just the same.

The Obsessive

The Obsessive is a bottom-line type of person, not one to settle for second best. He or she knows results are what count, and it doesn’t matter how you get them, just so you get them fast. In fact, he wants to get the stroke just right during the very first lesson. He stays after class talking to the instructor. He asks what books and tapes he can buy to help him make progress faster.

The Obsessive starts out by making robust progress. His first spurt is just what he expected. But when he inevitably regresses and finds himself on a plateau, he simply won’t accept it. He redoubles his effort. He pushes himself mercilessly. He refuses to accept his boss’s and colleagues’ counsel of moderation. He works all night at the office, he’s tempted to take shortcuts for the sake of quick results.

Somehow, in whatever he is doing, the Obsessive manages for a while to keep making brief spurts of upward progress, followed by sharp declines—a jagged ride toward a sure fall. When the fall occurs, the Obsessive is likely to get hurt. And so are friends, colleagues, stockholders, and lovers.

When the fall occurs, the Obsessive is likely to get hurt. And so are friends, colleagues, stockholders, and lovers.

The Hacker

The Hacker has a different attitude. After sort of getting the hang of a thing, he or she is willing to stay on the plateau indefinitely. He doesn’t mind skipping stages essential to the development of mastery if he can just go out and hack around with fellow hackers. He’s the physician or teacher who doesn’t bother going to professional meetings, the tennis player who develops a solid forehand and figures he can make do with a ragged backhand. At work, he does only enough to get by, leaves on time or early, takes every break, talks instead of doing his job, and wonders why he doesn’t get promoted.

The categories are obviously not quite this neat. You can be a Dabbler in love and a master in art. You can be on the path of mastery on your job and a Hacker on the golf course—or vice versa. Even in the same field, you can be sometimes on the path of mastery, sometimes an Obsessive, and so on. But the basic patterns tend to prevail, both reflecting and shaping your performance, your character, your destiny.

My Obsessive Path in Marathon Running.

In the past two years, I have participated and finished fifteen full marathons. I ran six full marathons in 2022 and nine in 2023 (Toronto, Fredericton, Halifax, Calgary, Manitoba, Regina, Quebec City, Victoria, Prince Edward Island). and two half-marathons (Mississauga and Montreal). In May 2023, I ran four full marathons back to back. It was gruesome, but I eventually pulled it through.

In running these marathons, I have learned many life lessons such as perseverance, persistence, endurance, resilience, and patience, to name a few. I reduced my full marathon time from 3:59 – 3:44 – 3:20. My present personal best is 3 hours 20 minutes, and I aim to run a sub-3 hours marathon later in the year. My sub-3 hours would make me qualify for the Boston Marathon later next year.

Training for a marathon and reducing my personal best by 24 minutes required becoming a little bit of an obsession. I trained like my life depended on it. I was in the gym for 854 hours 23 minutes, according to my Strava stats, and in a month like July, I was in the gym/trained daily, which amounted to 108+ hours of training. To achieve anything worthwhile, one has to be laser-focused and do the hard work required. As the saying goes, what is hard will eventually work if you work hard, but if you take shortcuts, you will be cut short.

My training regimen involved a lot of cross-training across multiple sports such as cycling, swimming, badminton, pickleball, strength training (weight lifting), lawn tennis and volleyball. These various sports helped with my endurance, flexibility and building my fitness core. It takes a lot of commitment to pull this up and consistency to see the end in mind.

It is not about the marathons but more about the life lessons and the man I am becoming while doing these hard things. I firmly believe that doing one thing is how you do everything. The self-confidence I gained from setting and executing these goals will come in handy as I execute other goals, such as learning multiple foreign languages or mastering programming languages and technologies (JavaScript, React and Python). It will get tough, and the plateaus will always pop up. The key is to remember you Why, keep at it, and you will eventually figure it out.

All the best in your quest to get better. Don’t Settle: Live with Passion.

Lifelong Learner | Entrepreneur | Digital Strategist at Reputiva LLC | Marathoner | Bibliophile |

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