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Should I Follow My Skill Or My Passion?


Chapters

0:0 Cal's intro
0:15 Cal reads a question about following your skills or passion
1:11 Cal's instinct
1:57 Lifestyle Centric Career Planning
3:6 The Basics of Career Planning
5:8 Discussion of #CareerCapital
7:27 Think about starting a hobby first

Transcript

All right. We have a question here from Career Opportunist who says, "Are there times where it is worthwhile to follow intimations of your career interest, even if you take non-trivial cuts in your career capital outside of the corner cases you've already mentioned in your book so good they can't ignore you?" Right.

There's some elaboration here. So we can get some context to this question. So Career Opportunist clarifies that he is a back-end software engineer at a large, well-known internet company who has built up quite a bit of career capital in that role. He then goes on to say, "My core interest in college, however, were in front-end client-facing work as opposed to back-end software.

I'm not tied to a particular job or passion. I just want to experience building user-facing software as opposed to just behind-the-scenes code." So he says, "I can either choose to become a more proficient back-end engineer, but it does feel like a less interesting route for me. But I could do that and focus instead on the opportunities to negotiate lifestyle improvements." All right.

So I don't have a definitive answer, but I'll tell you my instinct here. The grudging thing you put at the end, like I guess what I could do is even though maybe front-end stuff seems more interesting, I could get better at back-end engineering and focus more on lifestyle improvements.

I actually think that's probably the right answer. And it might not be the answer you want to hear from me, but I think at this stage of your career, the right thing to do, I'm going to guess, you haven't told me, but I'm going to guess you're at that critical stage, this roughly quarter-life stage in your late 20s, early 30s, where you're no longer starting out, you have skill, you have talent, you begin to have some options, but you're also not at that mid-life stage where there's other things going on in your life.

I would say at this stage, this is an important time to do lifestyle-centric career planning. I'll explain what that is in a second, but what I think is going on instead is you're feeling a bit adrift because again, you've got to that quarter-life stage where you found the job, you found the skill, you have some stability, you have some ability, and now you're thinking what's next.

And in our culture, and especially American culture, when I say our culture, we have this instinct that the content of our job is going to be the key driver of our satisfaction. So when you feel that initial tinge of malaise, because you've reached a plateau, your culturally trained mind immediately says, well, maybe if we shifted a little bit, the content of our work, we would no longer be adrift, we would break through the malaise.

So maybe it's back in software is the issue. And the reason why I'm feeling this malaise is that I really should be doing front-end software. I think if you make that shift, it would be kind of interesting, but you'd be back in the same place in a couple of years.

So now is the time to do lifestyle-centric career planning, which is what I think is the answer to that feeling that so many standard knowledge worker types feel around this part in their life. Now I've talked about this before, but the basics of lifestyle-centric career planning is that you identify what do I want my day-to-day life to be like in all of its attributes, not what do I want my work to be like, what do I want my actual life to be like?

And I want you to think about things like, where am I living? Am I in the countryside? Am I in a skyscraper? Am I in a small town? Am I helping my neighbors build a barn? Or is it I am having people over, commonly just shooting the breeze out on a front porch while people walk by?

Or is it I'm at a underground bar scene where there's interesting new poetry being done? Whatever. What is my day like? What am I doing? Where do I live? How much am I working? Am I getting after it or is work a small part of my job? Am I seasonal?

Am I spending six months a year not even working at all and doing other types of things and traveling around? These type of questions. What am I doing with my time? What about my character? What is my role in the community? What is the philosophies by which I live?

How deep is my existential grasp of my life? All of these type of questions. You fix this lifestyle. You feel it and you taste it and you imagine a typical week or day and something that really hits those intimations of, yes, this is right. And then you say, great, what are the paths to get there?

And that's where you build your plan. And work then fits into that plan. And work then becomes a mechanism by which you make progress towards this lifestyle that pushes all of these right buttons and really resonates. And that is where, as you enter this quarter-life period, your focus goes.

Aiming the ship that is your life towards the port that is a lifestyle that is deeper, that resonates with you, whatever those answers might be. And again, I keep emphasizing different people have different answers to these questions. It could look very different depending on the people. That's where I'd want you to put your energy.

Now, if you do this exercise eight times out of 10, you're going to find, oh, if I have a lot of career capital in something like back in software design, massively increasing that capital, because it's easy to take good capital and make it great than it is to go from no capital to good capital, massively increasing that capital quickly and using that as a lever to take control of aspects of my life and career is almost always going to be the right thing to do.

An example comes to mind from my book, So Good They Can't Ignore You, which you mentioned, there was a very similar character in that book, someone in a very similar situation to you. This was Lulu. And she was a back-end programmer. I believe she was databases, more like a database programmer designer, but similar idea, not front-end facing, worked for financial sectors.

As she got better and better at that, she said, what did I want my life to be like? And she used that as a lever to build a really cool lifestyle where she did six months on, six months off. So she left the company where she was. She went to a consulting role.

She was heavily in demand because she was great on this. She would do six months on. That's roughly enough time to do one or two engagements. She lived relatively cheaply, right? With her wife in Jamaica Plain. It was a cool, it's a cool neighborhood outside of Boston. They had this cool old house that they were, they were renovating.

And they weren't living lavishly. They weren't living in, let's go buy a really large, expensive house. So then you could spend the other six months doing interesting things and scuba diving. She got a pilot's license. Her family was from Thailand. So she would go do extended visits there. And it was just a really interesting lifestyle, but she figured out what she wanted.

And then she said, what's the best way to get there? Oh, I'm a great database developer. I can wield that to get where I want to get. So that is what I'm going to suggest for opportunities is do the lifestyle centric career planning, thinking and work backwards to say, how do I get there?

And then see where that takes you. So again, it's likely it might take you, uh, we'll tell you almost certainly take the skill you have out for a spin and use it to build a cool life. It might tell you, however, when you do this, like you want to be running a small startup that's front end facing and you live kind of cheap and you're living somewhere kind of cool.

So maybe it would put you to front end facing work, but it would be pushing you there for a reason. This is part of a big picture, not just an instinct that maybe this would make me happier. The final thing I will say, if you're interested in front end design, just as an intriguing intellectual challenge, even if this exercise has you stick with back end programming and using that as your main leverage, your main career capital lever, do some front end work as a hobby.

Build a front end facing website that you do as a side hustle or a side project that you build up and build up those skills, build it around something you're really interested in. You know, like you're a, uh, some sort of like super fan of the matrix or something like this.

I just watched that movie last night. That's what I'm thinking about it. Uh, Jesse's shaking his head. Um, you're a super fan of the matrix or something like this and whatever, or you're, you're really into some. I'm not good with this dungeons and dragons or something. I don't know, but you know what I'm saying?

Like, okay, build it about something interesting, fun, a community that you get some depth out of, uh, whatever it is. And you could get that experience as well. All right. So that's a long answer to a short question, because I really wanted to get to that bigger point, which is.

I'm increasingly a big believer in this idea that stage one of your career is figuring out how to be a adult in the world who's dependable and gets things done and starts to develop a real skill to get real career capital stage to. Deploy that capital towards a vision of the ideal lifestyle.

And then stage three is actually probably going to be much less career focused. You're in this lifestyle. It's going to be much more about yourself and self-discovery. I mean, I think it sets you up for the classic midlife crisis for it, not to be a crisis, but to be a time of actual discovery.

So that's my advice. Lifestyle-centered career planning underrated. Can't emphasize it enough.