The personal question my wife asked me that I can’t answer (and what it means)

I originally wrote this back in March ’15, but I decided to repurpose it a little bit because of recent events.

The Original Story

It’s been snowing/freezing raining in “The Metroplex” of Dallas-Fort Worth since basically about Tuesday, so this weekend wasn’t necessarily the best for outdoor pursuits or anything. (The Cowtown Marathon was cancelled, for shame.) I did some reorganization on Saturday (i.e. cleaned the house) and then figured, “Well, I should re-org my office too” (on a Saturday at 4pm). My wife and I went down there, re-org’ed my desk space and all that, and then when to get food/drinks. Still don’t really have friends in Ft. Worth (EDIT: now do!), so we were just chilling at this bar off downtown talking about a random assortment of shit (as people are wanton to do), and an interesting question came up as we were leaving. 

Here’s the basic idea: think of five (5) people who you’ve met at least once (or at least e-mailed with) and you look at some aspect of their life and say, “That’s cool. That’s successful. I’d like to emulate that.” Can you do it?

Mentorship

When you first hear the question, you might think it has something to do with mentorship, or this whole idea of finding/seeking a mentor. We know mentorship is pretty much dead — it fell at the foot of “The Busy Trap” — so when I first started turning over the question, I was terrified. I definitely don’t have any mentors professionally or personally (at least that I know of), so I can’t run too far down that alley before hitting a brick wall.

It might help to understand the moments that came before this question arising: I went to high school with a bunch of people, some of whom were great and some of whom were douchebags. (I basically could have written, “I went to high school” and stopped right there, no?) Yesterday morning I woke up at like 6am (couldn’t sleep) and as people do when bored/poking around, I went down a Facebook wormhole and found this kid I went to HS with. He’s closer to the douchebag category. Sophomore year I aspired to be friends with him, and he basically jerked me around a lot and we never really hung out. That was 20 years ago, so I don’t really give a shit about that now, but you know, because we put people in boxes, I still have him in the “douchebag” box.

On this Internet wormhole yesterday, I see that he’s just had a kid (not there yet personally), he works for some investment firm as an SVP or some shit, his wife works for Google, fucking nice place in Park Slope. You see where this is going? I have no desire for this kid’s life (I don’t even really understand finance, if we’re speaking honestly) and yet I’m looking at it all like, “Shit.” This is why there are studies about Facebook and depression.

So … what’s the wife question?

So my wife and I are discussing this, and she’s saying all the right things (good partnership!), but then we get to this question about kind of “What does success look like?”

And you know what? I don’t really know.

So I tried to think of five people, right?

The first place you go is your own parents. I think my parents are both successful for various reasons, so I guess I could knock off 2 there, although it feels a little bit cheap.

I started thinking about this guy whose book I read while I was in London, and then I e-mailed him, and he e-mailed me back, and now we have a dialogue going. He’s a consultant but he lives in an eco-friendly house off the grid in Madrid, and ultimately, kinda living off the grid and doing my thing and writing and talking to people about the future of work is something that may be cool. So I guess that could be No. 3, but I also just met this guy and we’ve only e-mailed, so that felt cheap. (EDIT: We basically e-mailed four times and that was it. Donzo.)

I thought about different bosses I’ve had, from 2003 up to now. Each of them has something cool/successful about them, so there were different options there, but there wasn’t anything where I was tangibly like, “Yes, that person for sure!” I’ve had bosses who I think shaped me as a professional (i.e. becoming more professional), those who shaped me in terms of skills (teaching me things), and those who just had a cool attitude. So there’s a mix there.

I thought about all my friends/acquaintances. I definitely have friends that make a ton of money, so some of them could be people. I have friends that make barely any money but are awesome, so that could be it. I had a couple of candidates there, but again, nothing like “Yes, this person for sure!”

I thought about my family and in-laws. Again, candidates … but nothing where I was like “Yes, definitely.”

Wait. What if I have no idea what success is?

So then I went down another wormhole.

Do I really have no idea what success looks like, or have no one who really personifies it for me?

This was kind of a terrible thought, which lead to a third wormhole of the day:

Do I mostly think of people as disappointing?

This is some deep psychological shit that’s probably a little too intense for a random WordPress blog, but I don’t have great self-esteem. Probably most people would see me as extroverted, but I personally don’t think of myself that way. I probably have a hard time letting things go and can easily be hurt by other people and how they act towards me. In sum, I’m probably a pretty fragile emotional case in a lot of respects. So that definitely colors this discussion. (EDIT: Since March ’15, I got fired and my life fell off a cliff a bit. But ’16 has been OK so far!)

In the end, I can easily get to five people on that list — but none of them (except maybe my parents) really jump out to me and say, “Yes, this is the path I should pursue!”

There’s an element of all this where “success” is a very broad term and it means a lot of different things to a lot of different people (kind of like the word “culture”), and I’m currently 34 and just got a job where I feel like maybe I’m doing something that makes a difference to the company as a whole — and I mean that’s the first time I’ve felt that way since I was probably 24 and teaching in the inner-city of Houston. (EDIT: Yea, so … I got fired from that gig.)

So maybe I need a little bit of time to define exactly what “success” is, and what models I think are interesting. That might be the case too.

And here’s a question for you: could you answer the above question quickly and easily? Do you have five people that for sure would be on that list? And don’t send me “Bill Gates” or someone unless you’ve actually connected with them. You can leave a comment or message me.

Thank you. I’m interested to hear your thoughts.