The Multi-Path Career | Hacker News Reader

The Multi-Path Career

jjbeshara.com

75 pointsswyx28 comments

Jack Dorsey has tried to be CEO of two companies and there seems to have been anemic leadership at Twitter. I'm not sure if execs splitting their time between companies so execs can make more money is really what we need.

> No, no, no. It’s got to be one company at a time, one job at a time. Right? Only investors can do that. [that= have a multi-career path]

Investors have a single career path: being investors. And you have a diverse portfolio you invest in: company A in AI/ML, company B in B2C, company C in biotech, ...

Similarly, as a C-level, you have a single career path: being C-level at [company]. And you have a diverse portfolio of project you invest in: geo-expansion, new line of products, internal reorganisation, raising money, ...

As an investor, to job is to find projects and teams to invest in, then let them do their stuff. By definition, the amount of time you will spend working inside projects you have invested on should be pretty limited.

As an executive, your job is to execute. And that takes a tremendous amount of time and energy. If you believe you are going to be able to execute well on multiple companies at the same time, dividing your focus and energy, all companies will suffer. AT some point, each company is going to need someone with 100% focus on that company. And person should be the one in charge.

The article goes off the rails right at the start when he compares having multiple career tracks to having a diversified portfolio. Diversified portfolios tend to have better risk-adjusted returns because their returns of individual investments are (supposed to be) relatively uncorrelated. Financial risk managers are always on the lookout for previously unidentified correlations between investments in their portfolio since that might increase the risks beyond what what has been agreed upon as acceptable with the clients.

The payoffs of multiple career tracks on the other hand are almost never uncorrelated. First off there is the obvious case that it is the same person doing all of them. This makes all labor-intensive careers very correlated in matters when a single event touches their health. Also, investment success of one stock usually means nothing (neither negtive nor positive) for other stocks in your portfolio. In most careers though, the payout of many careers is heavily tilted towards the higher end of the achievement spectrum and that may not be attainable without a full-time investment into that career. I don't think anyone would argue that an athlete dividing their time between three or more sports has a really good chance of becoming a professional in any of those, for example, because to be a professional athlete you need to be at the very top of the game and can't afford to spend 66% of your available practice time on other things. The correlation of these activities is actually very far from zero and therefore diversifying careers does not make sense from the start from an risk-management perspective. The rest of the article builds on that flawed premise.

One thing this new way of working opens up is it allows you to do something else at the same time as your main job.

It's a lot easier to switch to your side gig online shop when you're working from home than sitting in an open plan office.

I think the real gold is being able to investigate other things to do without any commitment. Just have a bunch of irons in the fire: negotiations with different people, PoC projects, that kind of thing, and see if any of them grow into something larger.

Depends a lot on what your main job is of course. But I would think a lot of office jobs have some sort of downtime where a quick context switch can be done thanks to being at home.

I really like this post. I've been noodling over a lot of similar career questions myself in light of the pandemic. All of a sudden, it became clear that I could just...bootstrap. With the rise of networks like Toptal and Facet, I get access to pretty high quality contracting opportunities and I don't need to commit to a "job" to pay the bills and make my money, which by proxy means I have much more time available than I used to.

Which means I can noodle around on that side business which all of a sudden...costs a lot less than it used to. Wonder how many other folks are in the same boat?

> Wonder how many other folks are in the same boat?

In the same vain. The time saved from my commute, I've been able to use those 2 hrs a day bootstrappig a low risk business opportunity at night. It's honestly worked well for me personally.

Awesome, congratulations! What kind of business is it -- micro-SaaS or something different?

I handed my notice in at my current job and ended up arranging a flexible ~2-3 hour a day contract with them. I used to commute for an hour both ways so I thought my day isn't actually any longer, but I get an extra chunk of money which helps a lot. If I was to leave my new job I could still afford to live on those hours a day anyway, so it's a nice backup if things don't work out.

That's pretty neat! Definitely buys you some optionality. Is there a minimum availability in days/week you need to make available?

Sorry I just saw this! Yeah we agreed a minimum average over a sprit of 1 day a week, but more likely 2 a week - I’ll see how I get on, I don’t want to overdo it

Just Curious: How has your experience with Toptal or Facet been, and how long have you been doing this (since the Pandemic)?

It's been pretty good so far. You still have to do the hard work with waiting for/choosing the right clients, but if you do that well, you get a lot of nice optionality from the network. I'd say it's well worth the time investment to join. I've been doing this for a couple of months right now from the consultant's side, but I've patronized their services on the buyer's side before, which was part of what got me interested in the model to begin with.

I worked as CTO of two companies for about a year. I tended to work a full day for one company then a full day for the other to lessen the context switching. It was hard work, but it was fun and very beneficial to both organizations. You really do focus on editing (what projects matter, what solutions matter, which candidates do we offer, coaching w 1x1s) which has much more of an impact than IC work. In fact, the only issues I ever had were classic time x resource tradeoffs, since I so little time for IC work.

How did the two companies do? I never understood how someone could hold two c level jobs at the same time. How do you handle all the work?

the trick is that the C work is delegated.

And what was the size/maturity/stage of the company ? Being "CTO" of a 5 person is very different from a 50/500/5000/50000 org.

And what was the focus of the company. Being CTO of "Algolia", or CTO of "Dollar Shave Club" doesn't really mean the same thing. (Both are great companies, but their tech needs are not comparable)

Both companies understood you were fractional? For those wondering, vCFOs and vCISOs are a thing where one senior level person serves several companies none of which could afford their services full time.

surprised to find this on front page. I feel like I posted this over 24 hours ago? and yet it says I posted it 3 hours ago. did it go in some sort of second chance rescue pool?

in any case fwiw I am not the author but I listen to his podcast. I also have some kind of weird hyphenate career - by day working at AWS, by night consulting for Temporal, and on weekends working on my book/indie making. Its a busy life but I'm finding I always have something to apply myself to and I have options galore. contrasts vs my mid twenties when I was just playing games outside of my day job.

There actually is a second chance pool, but you usually would get an e-mail about it.

for the record i didnt get an email about it. :shrug:

i figure you get an email if it was a Show HN that flopped or something. here i was just submitting an article i liked as a regular HN denizen.

I have a similar day job, and would love to start consulting on the side. Legal and worries that it could be seen as “conflict of interest” prevent me from starting however. How do you manage that?

i have an extremely unusual position as a contractor bc of covid so i am actually not technically a fulltime employee for the day job as well. so it works out there at least on the employment terms level. as for conflict of interest, it's a product they dont (yet) offer, its open source, and i'm performing a different role to the day job. i've been public about it and nobody's raised an issue on either side. ofc if you want to get nasty you could, in which case my downside is having to give up either gig. not terrible. its amazing what you can do with job opps when you dont need the money.

Anyone have a sentence to summarize the article?

Warning: the rest of this comment complains about the presentation style.

I really want to read this but at the moment I can't stand the Twitter/PowerPoint/BuzzFeed-esque bullet points, the subtitle says "TL;DR" and it's still TL;DR.

God fucking damnit, the state of the world, when people don't even have to be able to write coherent paragraphs (One sentence a paragraph! Just like in 3rd grade!) to have a lot of money that they can call themselves "angel investors"...

I had trouble reading this as well. It appears the author has trouble forming coherent thoughts. The article kept trying to pull in all sorts of directions all the time, a sort of lack of focus to do one thing: work on your point. (Ironic, perhaps?)

Good grief, YES!

> it will become the ideal work-style for executives

I personally don't believe in this. The executive role is already multifunctional - you need to were multiple hats on the same day or even at the same meeting.

The biggest problem most of the executives have is time. It is a problem even for a single company. I don't think any company is interested in a part-time CEO/CTO. Some exceptions are possible (Jack Dorsey, interim-CEOs) but no more than that.

However, for ICs this trend will happen. People are not limited by a location and can do Consulting type job in any location. It is a great opportunity for businesses as well - to hire part-time the best of the best.

There is a big difference between what an "executive" does at a 5,000-person company versus a 500-person company, and the latter (or even smaller, frankly) is where fractional leadership really makes the most sense. There are so many early-growth startups that could really use experienced leaders but don't have the funding and/or the track record to attract the kind of people they need on a full-time basis.

Disclaimer: this is a big part of what I do for a living so I do have some intrinsic bias toward it.

> There are so many early-growth startups that could really use experienced leaders but don't have the funding and/or the track record to attract the kind of people they need on a full-time basis.

I mostly know early-stage companies (10-300 people range). It is not easy to imagine how it might work on this scale. I'd appreciate some examples (job postings/blog posts).

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