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Summary and main question

Having worked in development for 7 years, reached what I believe to my ceiling, and being unhappy about having too many managerial responsibilities, I am looking to retire early from this line of career.

What should I do once I start living off passive income?

  • Start a career in a new space?
  • Volunteer?
  • Start a new organization?

Background and the plan

I am very privileged person, and around the age of 20, decided to orient my career towards doing the most good I can - not in a probabilistic, NPV kind of way, but based on social and economic development I can see and measure. This led me to set two 5 year plans for my career - the first aimed at acquiring skills in the private sector and building a good resume, then moving over to a social business; the second, to climb the ranks and grow my impact through managerial leverage. I will be reaching the end of the second 5 year plan and another key personal milestone by August 2026. 

The results and the problem

My current position is that of an executive managing an organization of 1,000+ employees which delivers $50M a year in measurable impact, growing 20-25% a year.

While not all this impact is attributable to me, I believe this is the most impactful role I may have in my whole life. However, due to my personality type (compassionate, but not empathetic; pragmatic altruist, but not into people directly), I am growing exhausted from managing an organization (people, ugh). I enjoy about 30-40% of my work (strategy, new projects, improving systems) but dislike the rest (hiring, developing, promoting, off-boarding, reallocating people, building alignment, etc.).

One reason why I am growing tired is that I fundamentally do not provide individual contributions anymore. I find myself very excited at the idea of coding a Python script, learning data science, tinkering electronics, and other nerdy things.

Personal situation and opportunity

I was both blessed and cursed by my family situation. By age 25, both my parents and all my grandparents had passed away - leaving my sisters to be my only direct family, but also setting me free and leaving me inheritances worth around $250-300K.

On top of this, I was financially savvy to save and invest, growing my net worth to currently $700K at age 31. Note that I donated very little of all this. At this rate, given my living expenses, I expect to reach my early retirement goal by Jan 1st, 2026 - meaning that I should be able to completely retire and live off passive income from these savings from age 32 until age 85-90. This is factoring in my family choices (married and in a childfree relationship).

This gives me the option to choose what to do with my free time.

Options

I have some ideas, but want to avoid motivated reasoning biases by getting third party opinions early on on what is the most impactful way forward.

Some options considered include:

  • Staying in my role or org - or do a lateral switch to a similar org - grow my managerial leverage even further
    • There is a material risk that I reach a ceiling where I cannot grow my impact anymore
    • I also risk burning out and completely losing my passion for impact, being jaded, etc.
  • Career reset - get started in a more sustainable career path, starting at the entry level / individual contributor. Sub options:
    • Earning to give eg. data scientist in tech start ups.
    • Stay in economic development eg. monitoring and evaluation.
  • Volunteering - using my skills to amplify others' impact.
  • Starting or joining a new organization - using my skills and some of my stash to start or join an impactful organization
    • This could eventually lead me to the same place that I am now, ie. becoming an exec and missing individual contributions.
  • Which path is likely to be the most impactful?
  • What else do you see?

Please critique my train of thoughts ! I welcome any and all external opinions. 

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Hi Barth, my very quick take would be that (if you hadn't already done so) there may be merits to reaching out to a careers advising org such as 80K Hours. I intuitively imagine that there are quite a few organizations that would benefit from either hiring or receiving advising from someone of your expertise, and that (e.g.,) 80K would be able to point you in the right direction.

Copy-pasting a comment I made after a careers event I ran* an events org  (*edit: reread this and realized I was illiterate) for EA Sydney (some of which may be relevant to you):
80,000 Hours 
- Career guide: https://80000hours.org/career-guide/
- Career planning series: https://80000hours.org/career-planning/process/
- Free one-on-one advice: https://80000hours.org/speak-with-us/apply/?referred_by=Elliot%20Teperman&referrer_Id=1231593241
- Jobs Board: https://jobs.80000hours.org/

High Impact Professionals
-Impact Accelerator Program: https://www.highimpactprofessionals.org/impact...
- Join the Talent Directory: https://www.highimpactprofessionals.org/find-a-job
- Professional and Workplace groups: https://www.highimpactprofessionals.org/groups

Animal Advocacy Careers
- Online Advocacy Course: https://www.animaladvocacycareers.org/course
- Jobs Board: https://www.animaladvocacycareers.org/job-board

Successif
- Career Services Application: https://airtable.com/apppnsBL2JjaU.../paghWMfYs63ePKfOv/form

Probably Good
- Core Career Advice Series: https://probablygood.org/career-advice/
- Personal Career Advising: https://probablygood.org/advising/
- Jobs Board: https://jobs.probablygood.org/

Consultants for Impact
- Career Conversations: https://www.consultantsforimpact.org/career-conversations
- Career Check-In Template: https://docs.google.com/.../1EP7gsZcCIFxV107mdhPB.../edit...
- Network Directory: https://www.consultantsforimpact.org/network-directory

A really good post on EA careers
https://forum.effectivealtruism.org/.../advice-for-early...

Thanks for recommending Successif! Our homepage might be a better starting point as it has more information on our focus on helping people reduce AI risk. That being said, the profile of the OP fits our program very well, and we would be glad to get an application.

A lot of the happiness or unhappiness that people have in jobs tends to be situationally specific. Thus, maybe if you took on a similar job at a different organization you wouldn't find it so burdensome.

With the enormous caveat that I don't know all the details about your preferences and life situation, I think that Staying in my role or org - or do a lateral switch to a similar org would be the best option. You preserve some optionality (you can always quit or switch if/when you feel that you have hit a ceiling), you are able to continue to build your career capital and your financial capital (both of which can be deployed for positive impact), there are benefits to being associated with an established organization (not just benefits/perks, but also networks, social respect, and the assessment/judgement that people make of an individual based on organizational affiliation).

If you really don't enjoy all of the coaching, delegation, and general people management that comes with your role (Your "people, ugh" comment made me laugh), then it will probably be challenging to find a senior-level role that you'd be happy with. A big part of greater authority, influence, power, and impact in organizations tends to flow through people. There are exceptions of course, but it does seems to be the most common situation. A few off the top of my head ideas:

  • Perhaps you could find some sort of subject matter expert role, where you are a senior-level technical specialist, and you don't have to do much 'people stuff.'
  • Or maybe you could hire somebody to tag-team some of these tasks with you. Many organizations have HRBPs, but you might be able to hire an executive assistant, or even to partner with someone so that you are able to offload some of the tasks that you dislike. Imagine if somebody else could handle even just 40% or 50% of the hiring, developing, promoting, off-boarding, reallocating people,  and building alignment?
  • There might also be some level of tailoring your role, if you speak to your manager and tell them that you enjoy the role overall but some parts of it are things that bring you down. Maybe your job responsibilities could be adjusted.

Unless you have a very special situation, I would lean against a career reset (from an impact-focused perspective). You might find it challenging for people to give you a junior-level role doing something that you have never done before, or something that you haven't been focused on for many years. Do you actually have the skills to be competitive as a data scientist in a tech startup (or in some other role?), or would you need to get a few years of training and then complete alongside fresh grads?

It is really hard to find a high-impact volunteer role.

Do you actually have the skills to be competitive as a data scientist in a tech startup (or in some other role?), or would you need to get a few years of training and then complete alongside fresh grads?

This is a crux.

Another factor to consider is that junior software engineering roles seem to be getting more competitive. I'm not sure how much of this is attributable to macroeconomic cycle stuff vs AI automation reducing demand vs increasing supply of people qualified for these jobs.

Thanks for reaching out about this, it seems like a task that others likely have too.

I know a handful of people who could retire soon, but instead stay active in the space.

At a high level, I really don't think that [being able to retire] should change your plans that much. The vast majority of recommendations from 80,000 Hours, and work done by Effective Altruists, wouldn't be impacted by this. For instance, for most of the important positions, money to hire a specific candidate isn't a major bottleneck - if you're good enough to provide a lot of value, then a livable/basic salary really shouldn't be a deal-breaker.

There are some situations where it can be very useful to basically do useful independent projects for a few years without needing to raise funding. But these are pretty niche, and require a lot of knowledge about what to do.

From what I've seen, most people who can retire and want to help out, typically don't really want to do the work, or don't want to accept positions that aren't very high status (as is typically needed to at least get started in a new position). These people seem to have a habit of trying a little bit with something they would enjoy a lot or identify with, finding that that doesn't work great, then completely giving up.

So while having the extra money can be useful, it can just as easily be long-term damaging for making an impact. I think it can be very tempting to just enjoy the retirement life. 

All this to say, if you think that might be a risk for you, it's something I'd recommend you think long and hard about, consider how much you care about making an impact in the rest of your life, then come up with strategies to make sure you actually do that. 

Personally, I think the easy thing to advise is something like, "keep as much money as you basically need to not worry too much about your future", generally donate everything above that threshold, then think of yourself as a regular person attempting a career in charity/altruism. The good organizations will still pay you a salary, and you can donate (basically) everything you make.

I'm not a career councellor so take everything with a grain of salt but you did publically post this asking for unsolicited advice, so here you go! 

So, more directly if you're thinking of EA as a community that needs specific skills and you're wondering what to do, your people management skills, strategy & general leadership skills are likely to be high in demand from other organisations: https://forum.effectivealtruism.org/posts/LoGBdHoovs4GxeBbF/meta-coordination-forum-2024-talent-need-survey

Someone else mentioned that enjoyment can be highly organisation specific and even specific to the stage of the organisation. 

My thought is something like:

  1. Take a year off and commit yourself to only doing exploration during the year, try out working in different organisations at different scales, maybe more early stage maybe later stage, I'm sure you got some knowledge on what is best here.
    1. Here's a fun book that mentions optimal exploration exploitation, I think of this a lot when it comes to my own life, it might be useful:
      1. https://www.goodreads.com/book/show/25666050-algorithms-to-live-by
    2. I thought this book was pretty good for a very specific strategy of quick career role exploration and how you can go about doing that:
      1. https://www.goodreads.com/book/show/26046333-designing-your-life
  2. Think about what roles that you can leverage your strategic people management & leadership skills whilst still enjoying the work? If you really want to do more coding then a CTO or similar role somewhere probably makes a lot of sense.
    1. Maybe you could work at a deep tech company?
    2. Maybe early stage startups is something you enjoy more, maybe you're more of a zero to one type of person?
    3. Figure out what it exactly is that you don't enjoy, you might be surprised, you might not be.
  3. Test, test, test. If you've found yourself able to do this in the past you have a lot of clout to be able to do it again, it is a lot easier for an executive to get investment again, know what people to hire, etc.
  4. I know a bunch of people who have felt similar things to what you're doing in this moment, specifically people in executive managerial roles. The pattern that I see from everyone is that take a break (shocker!) and then it really varies when it comes to how fast they get back into it again.
    1. Maybe there are specific mental health things you can improve that makes you 20% more effective at listening that can really help at the next thing?
    2. I like to think of it as them decompressing and learning the lessons from the past very focused period before getting back at it again.

Those are some random thoughts, best of luck to you! 

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I'm not able to provide much insight regarding the options you listed, but I want to make a quick note about reaching your FIRE number and potential future donations. If you decided that you need X dollars per year before you feel comfortable FIREing, see if you can have enough in investments so that you have a little more than X per year in investment income, maybe 1.1X or 1.2X. That way you would be able to generate ever-increasing donations without lowering your own quality of life.

Some previous thoughts I threw together a while back that might help a little bit: https://forum.effectivealtruism.org/posts/sbtdPJpeKDtYLr2Zf/joseph-lemien-s-shortform?commentId=AWaKkWjBpiAnrtRAC 

Are there roles in your current organisation that you think would be more enjoyable and could move into, say more at the level of making direct contributions?

Also, have you very thoroughly thought through the risks of retiring on $700k? I've seen in various discussions that it's common for people to think that a 4% withdrawal rate is likely sustainable to enable early retirement with low risk, but there are various reasons why that's probably optimistic, so just thought I'd flag it in case that's what this is based on. Maybe it's not...

I enjoy [...] strategy, new projects, improving systems

 

Maybe advising other orgs would be a good fit for this? E.g. advising startups in your area

Read some other comments, and career coaching from 80k sounds like a good suggestion!

Some other thoughts:

  • if you have an area that you care about already, you could do active work in this area
  • if you have not identified an area yet, AND it does not matter to you to work on things you care less about,  maybe find something interesting and relatively high paying for financial purposes and make monetary donations, or volunteering if you have time
  • I believe there are all kinds of combinations of the above!
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