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I've decided to begin publishing conversations between myself and others—with their permission—when I believe the conversations we have might be valuable for others. I'm happy to respond to questions, although I can't promise I'll respond to all of them.

If you would like to reach out, you can do so here.

Hey Brad! Wow, long time no see indeed. I'm so happy to hear from you. It's been forever.

I'm willing to talk with anyone about anything, so you're in good hands so long as what I say provides value to you. I'll warn you, though, I'm a verbose writer and your email inspired me, so I went all-in sharing my thoughts with you.

You'll want to read this when you have a few minutes. Grab a nice drink.

Searching for fulfillment at Asana

Fulfillment is a subject that's been on my mind a lot since graduating from college. Perhaps it's less surprising since I believe you and I are roughly the same age—I'm 27 currently—and we're both creative individuals.

While working at Asana, I frequently contemplated what I was doing, who I was doing things for, who I was, and what I was putting into the world. This coincided with, and perhaps informed, a great deal of existential dread. These feelings first arose due to boredom I experienced while working. By the time I got my job at Asana, I had been building websites professionally for over five years, so I had a short period of time to enjoy the "newness" of my job (this relates to a concept called the "hedonic treadmill").

I eventually became a person that did a particular type of web development at the company and was essentially "typecast" in my role. I'll admit that I could have done more to alleviate this point of frustration, but that realization only came from self-reflection after leaving the company.

In this complacency, I felt unfulfilled in my work and jaded towards my professional circumstances. I saw myself as a cog in a machine and I was dissatisfied with what I was spending my time doing. These feelings coincided with the first time that I reflected on capitalism. I began seeing my work as merely a means to an end for corporations to generate a profit.

I got depressed, smoked a lot of weed, and saw something I used to love doing—web development—as a burden, rather than an opportunity or passion.

I was discontent with my career. Asana offered a lot of flexibility and wonderful perks. Still, not having control over what projects I was working on, the circumstances surrounding those projects, and having no path for professional growth made me decide to start freelancing.

I hypothesized that the freedom I would gain from self-employment would provide me with circumstances to have a fulfilling career.

It did, and it didn't.

Freelancing is more fulfilling, to an extent

Freelancing alleviated many pains I experienced while working at Asana.

• I can take time away from work whenever I want
  • So long as there aren't projects I'm committed to working on.
• I can choose what projects I work on
  • This allows me to choose projects that encourage me to learn new things.
• I have greater control over deadlines
  • Clients can still be obstinate about deadlines, but I get to decline projects with deadlines I don't want to deal with.
• I make more money now than I did at Asana
  • I really didn't expect this to be the case. I also pay more taxes, so it's a double-edged sword.

If you had told me five years ago that I could be self-employed under these circumstances, I wouldn't have believed it.

Even with all of this, I'm still unfulfilled. What I'm doing, who I'm doing things for, who I am, and what I'm putting into the world are all questions that I contemplate regularly and I've yet to answer satisfactorily.

I'm still a cog in a machine, but I'm a cog that has slightly more freedom—both in terms of how I get to organize my work and financially—than other cogs.

Searching for fulfillment

Of course, like any good scientist, I have new hypotheses as I search for answers to these questions. My latest iteration on an "answer" to this question is that it's not what I do, but who I serve.

• I want to serve people, not corporations.
• Sometimes I want to be the "means to an end," while at other times I want to be both the "means" and the "end".
• I want to act out of desire, not obligation.
• I want to utilize my creativity as I experience it, not relegate it to my "free time" (don't get me started on the concept of "free" time).

I've thought about switching careers wholesale in the past, and I think it would provide some relief, but only for a period of time (back on the treadmill). I believe fulfillment comes from something deeper, aligning my day-to-day actions with my values.

I am fulfilled when my actions are a genuine expression of who I am, not something born from obligation.

I ask myself questions as a form of self-reflection. I enjoy capturing and elaborating on my thoughts over time. Here are some questions I've asked myself related to this:

• What do I value?
• Who do I want to serve in the world and why?
• What do I currently do that is fulfilling (/exciting /interesting, etc.)?
• What do I currently do that is unfulfilling (/unexciting /uninteresting, etc.)?
• What impact do I want to have on the world?
• If I could drop everything and do one thing right now, what would it be?
• How might I change my current circumstances to make things more fulfilling in the short term?

Will switching careers open the doors of fulfillment to you?

Probably not if you want to work in service of something other than shareholder profit. However, if switching careers allows you to authentically express yourself in a way that aligns with your values, who you want to serve, and the impact you want to have on the world, then it may be the perfect choice.