In Defense of Being a Jack of All Trades, Master of None

Right now, I’m known as someone who has a reputation for overcommitting. I am working during the day in special education while attending law school at night. I also write and maintain my blog in my free time, and am taking some courses on Coursera to supplement skills I’ve learned in law school. Whenever I have downtime, I train for marathons, all while trying to also spend adequate time with my wife and friends and maintain an adequate personal and social life.

Being someone with a lot of skills, but not quite being the best or a master at any of them has always been a part of who I am. I think a lot of people see this overcommitment and very diverse array of interests as a weakness, but it did not come overnight, and there’s a method behind my madness. I’m a jack of all trades, master of none, and most people don’t realize it is learned behavior and a coping mechanism from the disaster that comes from all my eggs being in only one basket.

For what it’s worth, I don’t think many people who see my performance in these various areas of my life would call me not a master in what I do. I am very close to the top of my class in law school (just outside the top 10%). At work, sometimes performance metrics are subjective, but I have been rated as a highly effective employee for years and have turned around compliance numbers and helped students grow multiple grade levels in reading. I go above and beyond for students and parents when it’s not in my job description and am, unfortunately, the person willing to send emails between 11 p.m. to midnight because I believe something is so important. I have qualified for the Boston Marathon in 2020, 2021, 2023, and 2024, which many people spend years training for.

The “master of none” label comes from my own standards and ambition. I do not want to be almost the best student in my class. I want to be the best student in my class. I don’t just want my students to improve significantly in reading — I want them to be on grade level if they’re very behind. I don’t want to be just someone who qualifies for Boston. I want to qualify for the Olympics as a runner.

There’s a question that Michelle Obama asked Barack when he decided he wanted to run for president: “when is it going to be enough?”

In truth, I don’t know. I can give an answer of “it’ll be enough when I become a federal judge” or something like that. In truth, the honest answer is probably never. I have never felt like what I accomplished is enough. I have never celebrated an accomplishment only to try to move towards the next step a few hours later. This restlessness comes from having ADHD, in part, my upbringing, in part, but it also comes from this deep faith in my ability to push past my preconceived limits and break free of a lot of internal self-doubt.

. . .

My tendency towards overcommitment has been a lifelong response to taking some parts of my life too seriously and seeing failure in areas of my life that I cared too much about as an attack on my identity. I am, by nature, very neurotic and obsessive over things I care about.

Right now, I am interviewing for jobs after law school at law firms. There’s an initial screening interview, and there is a subsequent callback interview if the firm deems you worthy for a second round of interviews, which then determines whether you get the offer. I have done a bunch of these screening interviews, but have gotten very few callbacks.

Naturally, I thought it meant I was somehow tanking these interviews or that there was some deficiency in my interview skills, which led me down a thought spiral thinking about whether I was personable or likable at all. My law school’s career office offered mock interviews to practice, so I did a mock interview and laid out all my questions and insecurities about whether I was coming off as completely awkward or some sort of freak in these interviews, or someone who was giving off some major red flags.

The mock interviewer said there were no red flags and no indication that I was disingenuous about my intentions. He gave feedback on my resume and what I should cut, and what I should keep. He said a lot of the time, factors outside the interviewee’s control at that moment dictate whether someone gets a callback interview or an offer. It can be the rank of your law school, your GPA, or whether your interest areas in a particular area of the law are the interest areas they’re hiring for. He told me to keep interviewing and not give up.

Still, I haven’t gotten many callback interviews, and no offers, which makes it very easy to feel discouraged. I sometimes check my email every five minutes, if left to my own devices. I start freaking out and asking my wife and all my friends what I’m doing wrong, and I fall into the trap of taking my lack of success in securing a post-law school position as an indication of my worth. A lot of my classmates also feel the same way, but waiting and freaking out about something that is, at this point, outside my control, is unproductive. This is especially true because I start to have negative thoughts of worst-case scenarios if I have not heard back in a few hours, and if I haven’t heard back in a day or two, it’s even worse.

The only effective ward against that type of thinking is refocusing on all the other things I have going on and attending to other priorities. I can complete filing tasks at work that I need to catch up on, or mow the lawn and take care of things around the house. Today, with a lot more free time on my hands, I have focused on improving my Excel skills and taking a project management course on Coursera for fun. If I revolved my whole life and mental energy around this interviewing process, it would continue to make me miserable.

But this is very minor in ways I can spiral, overthink, overanalyze, and make myself miserable.

. . .

When I was in high school, I took being a cross country runner very seriously. In fact, I took it so seriously that I saw it as the only important thing in my life. I wanted to be the fastest runner on my team, and the fastest person in the county, and you get the point. I just wanted to be the best and believed I could be the best.

And so I spent all day and all weekend thinking about running. I would obsess over trying to alter my form to be the best biomechanical runner. I overthought my diet and hydration. I would check results all day long, and sometimes I would try to sneak in extra training after our training ended for the day. I would obsess over getting the right running shoes, and as a frugal person, I bought way too many pairs of running shoes and racing shoes that didn’t really matter in the grand scheme of things.

As you can imagine, this came crashing down. I took running way too seriously. I put all my eggs in one basket, and it was entirely unhealthy. It’s not like I paid no concentration whatsoever to my studies and academics because I still did reasonably well in advanced classes. In fact, I would argue because I didn’t care and didn’t obsess, I did better in school than I did in some other years.

However, when I ran a race and had a bad day, it completely ruined my day. I couldn’t focus on school. I couldn’t even focus on video games. All I wanted to do was sit in my room and agonize. I felt like an abject failure, and tried to do hill repeats over and over again until I made up for my mistakes. I thought hard and hard over what I did wrong to bombard the race and train so hard for no good result. I will say one consolation prize was that, at the time, I believed any bad race was the universe’s way of telling me karma had caught up to me, and that I was being punished for not being a good enough person. I became a better and more humble person as a result because the adversity made me more empathetic, but always thinking I was being punished for a bad race wasn’t reasonable or healthy.

In truth, I didn’t realize this for years, but the problem was I cared too much, that I was working too hard. I put too many of my cards into being a runner.

This habit would continue for years. When running was going well, I would be full of myself and high on my own ego. I thought I was the man, and I would feel like nothing could stop me. But the same exhilaration had a similar despair on the flip side, and it wasn’t sustainable.

. . .

I learned from being a runner, and other endeavors where I went through this unhealthy cycle of going too hard and caring too much, that I could not just have one major endeavor in my life that I cared about.

Towards my senior year of high school, I disengaged from running for a bit. I started working on my school newspaper, hanging out with different groups of friends, and applying to colleges. In short, I had much more to focus on outside of running, so when I did not run well, it was not like I didn’t care, but I had other pressing priorities. In the grand scheme of things, my friends and my college admissions process was much more important.

There would be other times I cared about one part of my life way too much, including various times during my teaching career. But I never wanted one life endeavor to be the sole determinant of my happiness and identity again. As I’ve gotten older, I have made deep relationships and connections that define me much more than any athletic, academic, or professional accomplishments. I have my wife and friends who are like brothers, who I can talk to help zoom out any time I worry about shallow and materialistic life events, like these interviews.

I will say there are times when having a lot of commitments and being more of a generalist has served me well. As a teacher, I learned how to communicate better with neurodiverse learners, and how to treat every single person respectfully, but also establish boundaries and respect in other areas of my life. As a runner, I learned the importance of pacing and restraint in making it through a long day in other responsibilities. Because running has been such an intense and long endeavor that zapped a lot of my energy, the rest of my life feels like easy mode comparatively.

As a law student, I learned the precision of anticipating counterarguments and being clear and precise when making a claim or argument. Having multiple commitments across multiple domains has helped me think outside the box a lot more than I have before.

Above all, having something to fall back on has made me more versatile and nontraditional, but it has also made me a more fulfilled and happy person.

. . .

“You shouldn’t take this job,” a mentor once told me. “You’re not the kind of person who can take a step back. You go all in.”

I was applying to jobs at the time, and this was my mentor’s advice for one particular job. I interpreted it as a compliment. But I also interpreted it as a warning.

I have all these commitments going on simultaneously, and unless I emphasize them, people do not see that. They see me as the person that goes “all in,” even if I don’t feel like I’m necessarily going all in.

And that’s why it’s good to see myself as a jack of all trades, but master of none, because it’s a safeguard against my worst mental inclinations. When I am not a good teacher, I can fall back on being a good law student. When I am not a good teacher or law student, I can fall back on being a good runner. If I am not good at any of those things, I can fall back on being a kind husband and person, which are more important than any of those things. When my life is in utter turmoil, I have my faith to fall back on, and that reminds me to be grateful in all contexts.

I acknowledge I will never be the master I aspire to be in any of my endeavors. And even if I reach that goal, it will not be good enough. I will keep moving the goalposts to be higher and higher.

For the sake of balance, I am proud of being a jack of all trades, and believe it shouldn’t be thought of in the negative way it usually is. Being a jack of all trades might not be perfect. But it’s a lot better than obsessing over one.

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This post was previously published on Ryan Fan’s blog.

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