The Difficulty Of Finding A Good Job After Retiring For Years

The longer you are retired, the harder it may be to find a job if you want to go back. In this article, I'd like to share the difficulties I've faced finding employment in a new field. My situation should help folks think more carefully about early retirement and staying out of the workforce for too long.

In a previous article, I mentioned giving up on retirement for a variety of reasons. One of the main reasons is having more free time again soon.

Before each of my children was born, I promised to be a stay-at-home dad until each attended school full-time. My oldest is now in first grade and my youngest will be attending preschool five days a week in fall 2024. So the time to brush up my resume and look for jobs has finally come.

I don't regret giving up money, career, and status to raise my kids full-time. The time together, especially during the pandemic, was priceless. It was also necessary because we had a newborn with a nascent immune system. But I wouldn't mind having millions of dollars in lost wages since 2012!

Now I'm itching to return to work. It'll also be good to boost financial reserves to pay for exorbitant future college tuition. Goodness knows being an author is a labor of love and doesn't pay well.

Difficulties Of Finding A Job After Retiring For Many Years

Although I've been retired since 2012, I've also been consistent in publishing on Financial Samurai. Therefore, I wouldn't say I've been checked out by any means. If I was, then finding a job would understandably be more difficult.

But it's been eight years since I've done some part-time consulting for private tech companies. And part-time consulting is as close as I got to traditional work without actually doing traditional work. Eight years away from traditional work is an eternity.

Let me share some difficulties about my job hunt journey to help you better prepare for yours. I'll also advice after each point.

1) Not many warm connections

The easiest time to get a job is when you have a job. Having a job signals an employer values your work, so it's easier for other employers to take a chance on you. Employers also tend to covet what their competitors have.

Given I've been out of the workforce since 2012, my work relationships are thin-to-none. I can't easily call a buddy to make an intro to the hiring manager of a job that I want. A large percentage of highly coveted jobs are obtained through referrals.

Blindly submitting your job application through a company's online job portal is an inefficient and difficult way to land a job interview. You're just wasting your time as nobody will bother to even acknowledge your application.

My main network is now through tennis and pickleball. But many of these folks are retired, underemployed, or working in fields not relevant to me. I haven't tapped my network for introductions, but I probably will in an upcoming newsletter.

Advice: Maintain relationships with people in your previous industry after you retire. Spend at least a year networking with people in a new industry you want to join before you start applying. One coffee, meal, or outing a quarter per person should suffice.

2) The fear of being too old to be accepted

When I left work, I was 34 years old. Today I am 46 years old.

One of the reasons why I wanted to work until 40 was because I realized back then that there was age discrimination in the workplace. As a manager, I had to go to diversity training. And one part of diversity training was being aware of ageism.

I figured, no matter how much training there is, people will always be biased, unconsciously or consciously. I didn't want to have to deal with ageism so I committed to retiring by 40. Kind of sad right?

As I was applying for jobs, I noticed time after time there would be an optional section in the application about race, sex, and age. Naive as I was, I filled everything out.

Below is an example.

The difficulties of finding work after retiring early - ageism

Did you notice something interesting? The highest age category is 45 or older. On the one hand, “45 or older” is better than “40 or older,” as it is more inclusive. On the other hand, there is an implicit assumption that once you're 45, you're part of the oldest category of working people.

Why not continue to break down the age group every 10 years to 45-54, 55-64, etc? After all, the majority of Americans retire in their 60s, not 40s or 50s. The “45 or older” checkbox immediately made me feel old and brought back my fear of ageism again.

Advice: Skip the demographic surveys or questions about age, race, and gender if they are optional. If they are not optional, then you have to tell the truth. Unless you're an underrepresented candidate, accept your answers may hurt you.

3) Competition is fierce for the hottest sectors

Since writing my post about going back to work, I've thought long and hard about what I want to do. Originally, I had thought about joining the Golden State Warriors as a video coordinator because I love basketball, strategy, and competition. However, traveling from October through April and beyond is too much time away from my family, so I dropped the idea.

Then I had an hour-long conversation with Ben Miller, CEO of Fundrise, about their Innovation Fund. We talked in depth about their investment in Databricks, artificial intelligence, and venture capital.

My conclusion was that if I'm willing to invest money in the Innovation Fund and several other venture capital funds investing in AI, I should also be willing to work at one of these companies.

If you are currently working and aren't willing to invest in your company, you should probably find another job! Here's my conversation again about investing in private innovative growth companies.

AI Is Ultra Competitive

My problem is that the AI sector is hot, hot, hot! An endless number of highly motivated, smart, and connected people also want to work in AI because it is a technology that will have a massive impact on our future.

Personally, I'm most excited about how AI can accelerate science research to come up with more cures for illnesses and disabilities. Using AI to more efficiently test genome therapy to restore vision in millions of people sounds incredible.

Similar to applying for student admission to elite private universities, there are hundreds, if not thousands, of qualified individuals per spot. There's little chance of landing a job at a top AI company without connections or a tremendous amount of luck.

Advice: Try to identify companies and sectors that could become hot and apply before they do. Alternatively, apply to companies below the top tier that are not mentioned in the media.

4) The pay has to be worthwhile

I took an assistant high school tennis coaching job for $1,000 – $1,200 a month for three years for three months a year because I also love tennis. As a new boy dad in 2017, I wanted to understand what it was like to mentor teenage boys so I could better prepare for when my son was a teenager. Further, I wanted to understand what made this particular high school so desirable.

However, to work at a traditional corporate job requires traditional pay and equity. Given my base salary was $250,000 when I left my finance job in 2012, I've anchored toward earning at least $250,000 in base salary at a future job. As a result, the number of jobs that pay such a salary is still not high. In addition, I do not want to go back to banking.

The only jobs I'm most interested in taking are business development jobs at AI companies. Given many of these AI companies have raised a significant amount of funding, they have a greater capacity to pay. Unfortunately, the higher the pay the greater the job application competition.

As a retiree looking to go back to work, you either take any job because you're bored and want to be a part of a community. Or, you might have high expectations because you are only willing to dedicate your time to something extremely worthwhile. In the latter situation, if you aim too high, you might end up single for the rest of your life.

Advice: Assess the tradeoff between pay, the job experience, and what you can get out of the job besides money. High pay might also be associated with more work and stress. Perhaps you can find a lower-paying job in an attractive industry that provides a greater work-life experience.

5) Getting a job is a numbers game

Getting a qualified lead is a numbers game. You might have to evaluate 10 real estate deals to find one incredible investment. As an author, you might need 100 people to sign up for your newsletter to have one person buy your book. As a person looking for love, you might have to go on 50 dates before you find a suitable match.

The same concept goes for finding a job. The greater the number of jobs you apply for, the greater your chances of landing a job interview and an offer. The funnel might look like 70 applications, 3 interviews, 1 job offer.

As a retiree with a comfortable amount of money, you may not have the stamina or the sense of urgency to apply to as many jobs as you need to in order to land one. You might naively think that with your outstanding experience, all you need to do is apply for your top 3-5 jobs at the very best companies. This would be a mistake.

Advice: If you're serious about getting a job, apply for as many jobs as possible every day. Don't stop at five. Keep going until you hit 50, then 100, then 200. Do not be deterred by the rejections or non-responses. Fill the top of your funnel.

AI Jobs In San Francisco Are Everywhere

I'm fortunate to live in San Francisco, one of the highest income cities in America, because so many AI companies are based here. To be able to just take a bus downtown to meet with prospective AI employers or go to AI meetups makes things much easier.

Firms such as OpenAI, Anthropic, Databricks, Snowflake, and a bunch of AI-related companies are all in the Bay Area.

However, I've failed to build a network of people who work at AI companies. In addition, I failed to recognize the promise of AI before 2023. As a result, I need to get busy meeting more people, go to more events, and learn more about the industry.

Back in 2012, when I was applying to private startups, I faced the same issue. I had applied to Airbnb when it was valued at only $3 billion. I felt strongly that Airbnb would grow to be enormous. But I had no connections so I couldn't land a job. At least their Friday happy hours were a lot of fun!

Tech job rejection letters - AirBnb rejection in 2012
One of three Airbnb rejection e-mails in 2012

Late At Recognizing Great Job Opportunities

What I realize now is that plenty of other people recognized Airbnb's potential in 2012. I had a narrow field of vision, where I believed I was part of only a few people who recognized Airbnb's upside. The reality was hundreds of people likely applied for the same jobs I was applying for back then as well.

After about the 50th non-response or rejection by various startups, I gave up and accepted my new path as an early retiree. I would travel frequently over the next 12 months while concurrently writing online.

Then I spent between 15-25 hours a week for a couple of years consulting for Empower (previously Personal Capital) and a couple of other firms before taking another long break again in 2015.

Long-Term Commitment To AI

Although my success in finding a job in AI has been unfruitful so far, I've also just begun my job search. I have until the fall of 2024 to find that ideal AI job because that's when my daughter will begin preschool full-time. By that point, it will be very difficult for me to stay retired.

I spent 11 years at my old firm and have spent 14+ years writing consistently on Financial Samurai so far. Based on my history, if I find a suitable AI job, I plan to dedicate at least at least five working. By the year 2030, my son will have to apply to high school. At that time, we might relocate somewhere else, like Hawaii or Taiwan.

10-20 years from now, I don't want my kids asking me why I didn't invest or work in AI today. If I don't end up with a job in AI, then at least I can point them to this post and all my rejection letters that Dad tried. Here's one of them. Whoo hoo!

OpenAI job rejection response

Building Investment Exposure To AI

I know my ability to get a well-paying job at a promising AI is going to be difficult. I assign less than a 5% chance. Therefore, I will build investment exposure to AI while looking for a job.

I will invest $500,000+ in AI companies through venture capital funds over three years. If AI performs well, then in 10-20 years, the $500,000 may grow to $2 – $10 million. The return would be a hedge against me failing to get an AI job and my children failing to get a job they desire due to getting crowded out by AI.

If my $500,000 investment in various AI companies doesn't pan out, then AI will have likely turned out to be less impactful than anticipated. In such a scenario, I will have saved a lot of time by not working at an AI job and my children will likely have found gainful employment. What a win-win!

So far, I've committed about $700,000 to various venture capital funds (excluding private real estate funds). But only about 20% of the exposure in these funds is to AI. Hence, I've got to either find funds that take more concentrated AI bets or invest more capital overall.

The Innovation Fund likely has over 30% exposure to AI because it invested 25% of its fund in Databricks recently. I will build a portfolio of private funds over the next three years and ride this trend for the next two decades.

A Better Back-To-Work Strategy For Retirees

Retiring or retiring early can be an extremely nerve-wracking decision. It was only after successfully negotiating a severance package did I find the courage to leave. Otherwise, I almost certainly would have kept grinding until at least age 40.

If you're considering retiring early, but are not 100% certain whether retirement will suit you, I recommend you do one of the following to hedge:

  • After retiring, consult part-time until you feel more than 90% certain staying retired is the right move, then stop consulting
  • Keep consulting for the entire duration of your retirement to keep your skills and connections up to date
  • Retire for two or three years, consult for one or two years, take a break and either consult some more or quit consulting altogether once you're comfortable with retirement
  • Retire for two or three years, unretire and get a full-time job for two or three years, and repeat the process until you're certain you no longer want to work

After three years of not working, your prospects of getting a job at a similar pay and level to your previous job declines dramatically. Therefore, you want to avoid having longer than a three-year gap in your resume.

Although I have been able to do what I wanted since 2012, I am now paying the price for not being a soldier. As a result, I may have to settle for less money or take on a job that is not ideal in a different sector.

Let's see what the future holds!

Reader Questions And Suggestions

Anybody retire and try to find work again years later? How did the process go? What would you have done differently? Anybody work at OpenAI, Anthropic, Databricks, ReclaimAI, Hive, etc that could give me a warm intro?

If you're looking to retire early or leave a job with money in your pocket, pick up a copy of How To Engineer Your Layoff. It will teach you how to negotiate a severance so you can do what you want. Use the code “savefive” to save $5 at checkout.

How to engineer your layoff - learn how to negotiate a severance package and be free

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About The Author

98 thoughts on “The Difficulty Of Finding A Good Job After Retiring For Years”

  1. I retired at 62. I returned to work two months after my retirement. My new career is totally different from what I was working in. I retired at 62 because the firm I was working for was setting me to get fired. I probably should have allowed them to fire me. Instead, I retired. I work part time now. I decided I did not want to wake up some morning at the age of 85 and realize I needed to go back to work. I realized that if I need to go back to work at an older age after being retired for a long time, very few would want to hire me. I am not the kind of person who can just dive into cold water. I need to gradually get used to a new life.

  2. Sam,
    This is a good post. It’s real.

    Sometimes re-entering the workforce means leaving the corporate world and simplifying the new position.

    At 54 I started a crew member position with Trader Joes in Nashua NH. My wife and I had recently built a home & moved up here from the Boston area. With a new home and plenty to manage my wife continued here working from home position, I got a job 5 miles away. New home, 2 dogs and more… I didn’t have the capacity to be immersed in the corporate sales world with travel. I go to work and leave it there at the end of the day.

    Everyone is different, we came up with a plan that worked for us. Thank you for sharing your story.

    All the best,

  3. I have always enjoyed your content, thank you. I am outside of your demographic, as I am older – I use it to send tips to my adult daughter and others.

    I couldn’t help the dilemma you have of going back into the workforce, is not dissimilar to anyone that has taken time off (typically women) to get back into it – it’s a ramp. Perhaps some parallel to this in a future piece of content.

    Also, an idea, rethink the last 10+ years as retirement, what you are doing (or had been doing) isn’t retiring as much as self-employed or entrepreneurism. Isn’t it possible that traditional careers of continuous W2 or only self-employed or sharing economy, are ending? Perhaps they are just phases we are going through – just an idea to noodle around. I have read your content with investing and other things, and I am not sure I would classify it as ‘retired’ – just a different way to earn.

    When I was in my early 30’s, I set a goal of retiring at 55. Now at 54, with 8+ months to the goal, I could easily retire. I now work for myself, with the goal of keeping my working time 20 hours or under (I do it because I enjoy the work and social connections). I think everyone should strive for financial security and then work on their own terms – whatever that looks like.

    Good luck.

  4. Hmmm. After all the bluster you are selling out. I wish you luck, but your credibility has taken a hit in my opinion.

    Enjoy the grind. I look forward to seeing your post in a year or two when the market comes back and your post “going back to work full time was a mistake” comes out…..

    1. Thanks Matt! Yes, I have lost credibility and failed at FIRE. Life is unpredictable and I’m doing my best to roll with the ups and downs to best take care of my family and live life with minimal regrets.

      At least I had a good 11 years, and maybe 12 years if I can get a job in the fall of 2024.

      I appreciate that you’ll continue reading in a couple years and telling it how it is. How is your retirement lifestyle going?

      1. At least you are being honest and transparent. I appreciate that.

        Just be aware you have inspired a lot of people who might not know what to think about your last post and how they might act in their own lives moving forward.

        I have enjoyed reading your posts as it gave me encouragement when I made the decision to not actively work traditionally.

        It is really hard to deal with people/society not understanding why one could not work, be a normal person, neighbor, etc.

        I’ve enjoyed your newsletter and will continue to read it. When you re-retire I’d like some fresh seafood delivered to my house. If you go past 2 years I will send you a Chicago pizza.

        Samurai needs to sharpen his blades……

        1. Matt, I’m curious if this is how you speak to others in person? Because if it is, I suspect you will encounter difficulty building relationships.

          Why be judgmental to Sam who is sharing his honest journey and trying to help others uncover any blindspots about retirement they might have?

          How does one lose credibility by sharing their journey, both good and bad? Would you rather just have someone say everything is perfect and how they make a lot of money and are crushing it all the time?

          I, for one, appreciate the transparency of Sam’s journey. Do you think he owes you something? How about just be happy enjoying your life with your wife and kids. Unless, family is what you are lacking. If so, the first step is treating someone with respect and kindness.

          1. Andy, please make sure you read my second comment and Sam’s response to the first.

            Sam always asks for comments. I was genuinely taken aback by his last post.

            I don’t often comment on posts of any type. I’ll leave it up to Sam to decide if he was offended or not.

            1. Hi Matt, I’m not offended, but I’d rather grab a beer with someone else.

              Do you have kids and a spouse? What age did you retire and how old are you now? What do you do with your free time?

              Criticism is fine. However, some background would be nice to know where you are coming from. Thanks

          2. I would be shocked if Matt has a wife and kids. Based on his comment, he sounds very insecure, which makes it hard for anybody to want to be friends or be with him.

            Clear case of projection.

            1. Yes Derek, you are correct. I’m infertile and incapable of having a wife based on a few quotes you didn’t care for. Lighten up Francis

              1. Sorry to hear Matt. If you don’t have looks or fertility, work on being social if you want companionship and a family. Having money and retiring early is pointless if you’re not enjoying life and helping others.

                You sound miserable and alone, which is probably nobody to blame but yourself.

  5. Sam,
    I’ve had the same trouble as you in my job hunt. I retired two years ago at age 55. I was highly skilled like you, as an Actuary!
    I decided to pursue my lifelong dream of being a cop (because frankly at my age, my level of fitness-which is tip-too, does have a shelf life). I was hired by my local Sheriff’s Dept and they sent me to a grueling 13-week law enforcement academy. I soon realized this isn’t for me at all and I was completely disillusioned because in today’s world, cops aren’t allowed to be cops! I should have pursued this 30 years ago and I’m kicking myself in the butt for making this decision now.
    So I quit after only 3 weeks of fulltime patrol.
    I opened a LinkedIn account and I have applied for several jobs in my former field, even attempting to take jobs that I’m overqualified for.
    No one has offered me anything. Maybe because of my age… ?
    Some companies were put off by the fact that I went into law enforcement. Can you believe that! I grew up believing that we should respect police as their calling is an honorable one.
    I’m very frustrated and don’t know what to do at this point. Any suggestions would be greatest appreciated. If you find my story of interest, you can share this in your blog, but please only use my initials.

  6. Have you considered working with some of the incubator companies? Even if your core skills in finance are a little dated, you have a wealth of other skills and knowledge that could be helpful to startups.

    They may pay little to nothing, but they can be a low friction way to reconnect and meet people in many segments.

    Good luck!

    1. You actually make the case for me not wanting to move to Hawaii then! I want the rest of my life to go as slow as possible so I feel like I have more time and can’t live longer.

  7. I have been trying to secure a meaningful position in my career field for over ten years now. My industry is booming and they are hiring everyone that they can get their hands on with the exception of myself. My issue is that after being laid off more than a decade ago I figured out how to support myself without the need for outside employment. I expected to be welcomed back once my industry recovered. A part of my struggle is that my expectations are too high. What I will accept has been tempered by the knowledge that I can comfortably remain where I am at. I had no idea how much self-employment would contaminate my opportunity stream. Being older does not help either.

  8. Buddhist Slacker

    Dude, you need to apply for AI jobs in the finance sector. After you get one there, you have a better chance of moving to your desired industry. It’s going to be super hard if not impossible for you to get a job in healthcare related industries without an MD or health science or science related degree and clinical experience. Just like that guy said you need a CS degree for AI bizdev or presales in tech, you need an MD degree for pretty much anything in health care that’s not grunt work. You’ll be competing with all those doctors with MD’s + JD’s + PhDs with years of clinical experience plus industry and government connections. So you need to get your foot in the door in an industry where you already have cred.

    Many years ago, I dropped out of tech for a year and a half. This means that I was obsolete after that year and a half. After taking grunt jobs, I quickly moved my way up and now I’m in an IT related job again. So don’t fear the grunt job. A grunt job is a great low stress way to get your foot in the door. If you deliver results and work your butt off, any manager, even a manager in government, will promote you.

    Also, knock a few years off that resume. Don’t put the early jobs. You can DM me if you want some more extensive advice on reentering the job market. But I think you already know what you need to do.

    1. Thanks for the detailed response. It’s great to hear unvarnished experiences from boots on the ground. Many recommendations out there in blog articles or YouTube videos are full of observations cherry picked to make the writer look good or subject to survivor bias.

  9. Stay Retired or build a new biz

    For what it’s worth…..
    The Age Discrimination in Employment Act (ADEA) forbids age discrimination against people who are age 40 or older. It does not protect workers under the age of 40, although some states have laws that protect younger workers from age discrimination. It is not illegal for an employer or other covered entity to favor an older worker over a younger one, even if both workers are age 40 or older.

  10. Is that Anthropic application for real? Aren’t those questions illegal? And even if they are “optional” why would Anthropic open up themselves to liability through the perception of impropriety?

    1. Yes, they are real, but optional questions in the job app.

      Given it is optional, don’t think they are at risk of impropriety. But the age categories highlights how the company thinks.

      1. Any hiring employer that has a preference for younger employees can easily screen out older candidates in myriad ways without violating the Age Discrimination in Employment Act.

  11. Great post again Sam, I left the work force in 2020 and was willing to return back to the work force in 2021. I applied for a lot of jobs and interviewed for a lot of them. I was offered a couple of positions, but they were not a good fit for me after consideration. I make nearly as much money as I did working when I consider the costs of working so I declined the positions.

    I am not concerned in the least about finding some kind of work should I need it again. I am in a much better financial position than almost anyone I know and with Treasury yields being high it is acting like an early pension for me. I have a government pension that will start paying out in a few years and then Social Security. A lot could change from now until then, but I can’t worry too much about that because none of us can control the future and is anyone’s job really safe nowadays anyway?

      1. The government pension system is kind of weird and backloaded. The longer you work the more payout the pension gets so that kind of appealed to me. That being said I haven’t needed a paycheck for a long time so the thought of doing exactly what I did before was not appealing to me. I applied for jobs to try and move up in my field. I taught junior high and wanted to move to high school. I applied for tons of high school jobs which I am qualified for, but the only offers that I received were from junior highs again.

        There is not much room for advancement in the education world nowadays and I have no interest in being an administrator in schools nowadays. That is the most boring job I can think of.

        I changed my portfolio allocation in late 2021 to have a 50/50 balance of stocks and treasuries. That has generated about $40,000 in income for me each year since 2020. I only spend about $20,000 per year. So I still have excess capital. I don’t have any work related costs and no FICA and union dues to pay so my income hardly changed.

        The treasuries are delivering about $2000 a month in income at current rates which I didn’t expect when I left my job. My dividend stocks generate another $10,000 or so and my trading in 2020 and 2021 in my individual brokerage generated another $10,000. Last year was bad for 401k and my individual brokerage, but I am in the green now again this year in a big way. Nvidia and ASML have been big winners for me.

        I don’t really care about short losses in the 401k because I won’t touch the money for another 10-15 years and it is well diversified in growth, value, index and International funds. The value stocks did awesome last year and really helped offset the losses in growth that everyone had.

        I know it was a long answer to your question but I left my career because I didn’t want to do it for the next 20 years and I wanted to move up to a better position and couldn’t. I have worked to get financial knowledge and skills and I will use those to generate money in one form another until my pension and Social Security arrive. I have every confidence I can generate enough money with what I accumulated. I am single and only responsible for one person.

  12. What you’re looking for is tough without a computer science degree or silicon or software background. Most Bay area technology BD jobs have a CS/EE degree as a req. I work in software engineering services and have an active Gen AI sales pipeline but it’s still early days for serious revenue from Gen AI. Our company just nutted up for a really cool AI certificate program from Kellogg/Northwestern – they’re making mandatory for Dirs and above. What you’re looking for would also require min 50-60 hr work week. I do feel you retired too young as I’ve found 2+ decades in high tech has taught me a lot about myself that I’m not sure I would have discovered otherwise or too late but I would have made the same choice if my net worth was what you had achieved at 34. Now in my mid-50s I’m a little torn about retiring as AI will be a huge software oppty for me but I want to indulge my athletic hobbies of golf, surfing, snowboarding, yoga, gym while my body is still healthy and injury free. I could easily play golf and surf every day (except my golf club is closed Mondays) or snowboard in the winter then come home and chase my wife around the house. My timeline is 5 years, and I greatly look forward to not using my brain to make a living and focus all cycles on my mind-body connection for personal, relationship and athletic optimization. And I feel incredibly fortunate to have so many hobbies to pursue when I retire, all of which I have invested decades into.

    1. Didn’t realize business dev requires a CS/EE degree. I thought you just have to understand the value prop to sell.

      Given you’re in a coveted AI seat, you might as well work at least five years to see if you can make a larger fortune and ride the wave.

      For folks like me on the outside looking in, we’ll just have to be investors or spend our time on our hobbies or other interests instead.

      50-60 hours a week is a lot. Based on the folks I see working while playing pickleball midday, I don’t see how that many hours is possible.

      1. Most tech sales/BD requires CS/EE degree – basic screening criteria as those are always among the toughest majors and easier to sell a technical product if you have some capacity to undertsand it, which without having the academic knowlege you won’t or at least your knowledge if self taught won’t be credentialed. Consulting firms also want those majors. Even Wall St as traders now have to write code. I got a CS degree and went straight into sales, which blew the minds of my techier classmates. Go look at the CVs of tech sales leaders and you’ll see lots of CS/EE degrees.

        The top AI company NVIDIA is an absolute slavedriver mentality especially in sales. Any startup is well north of 60 hrs a week. You can play Pickleball during the day but you’re on email until laaate.

        5 yrs is my target for sure but I would not be opposed to pulling it in if I can. Too much fun to be had especially once we move back to South OC and I can go to the beach as Bay area beaches suck. Great waves up here but at least in Santa Cruz they don’t keep the beaches clean and outside of Oct/Nov its usually in the 50s.

      2. Buddhist Slacker

        Sam, in order to sell someone something, you need to understand their current problems and speak their language. That’s why you need those degrees, industry experience, government connections, etc. Also, trust me, healthcare has more jargon and acronyms than tech because it’s so heavily regulated by multiple regulators. In that way it’s similar to finance except there are more health care regulators and those regulators have teeth, unlike the SEC and HUD for example. Think of all those finance regulations you missed out on implementing. I also used to work in banking.

      3. > 50-60 hours a week is a lot. Based on the folks I see working while playing pickleball midday, I don’t see how that many hours is possible.

        Those are not the competition you’ll be up against when applying for the AI jobs. The younger candidates are eager to jump onto the latest bandwagon (which now is AI), are either fresh out of school or have ample time to take extensive online instruction, and are willing/able to work 60+ hours a week — as evidenced by their extensive github profile and portfolio projects. I’m curious what is the demographic of your fellow pickleball players?

        1. What you say could be true.

          I play with a lot of 25-35 techies working at home at the pickleball courts.

          But maybe they are not the A-players and are more cruising and happy with being in the middle. Which is fine.

  13. Seems like even most rich people have jobs (it must be hard to be fulltime playboy). The difference being that they work at what they want to work at, where they want, when they want, and only as hard as they want. I retire very soon, which is good, because I’ve become very bored with what I do (mostly waiting around to show how wise and experienced I am when the need arises–but I pretty much prevent those kind of needs from arising just by anticipating them). The money is great, but I’m tired of being tied to an office, even with a VPN. Pretty sure they are going to plead with me to work part-time, even remotely, after I break the news here. But if I go back to work at all it will be something like writing more fiction, because I can control everything about that and don’t need the money (not that there is much in that if you aren’t a household name).

    Of course, if Harvard’s Church (or Calico, or others) do what they are strongly hinting that they can, and extend our lifespans by another century or two, it might take more than that. In that case, I might consider going back to school to try something totally unrelated to anything I’ve done for money (because it wouldn’t be for money), possibly becoming a physicist, or a screenwriter/actor, or an architect, or whatever.

  14. I’ve been working in AI (specifically “Natural Language Processing”) for almost 20 years. We’re not hiring at the moment so I can’t be a direct asset to finding a position, but if I can be of any informational help feel free to ask here or via email

    1. No problem.

      Has it gotten more fun and exciting recently? 20 years is a long time, so surely the work must be intriguing.

      Has your career in AI been rewarding? It terms of impact to society and financial?

      What are the downsides of working in AI?


      1. Yes, it’s more exciting recently – LLMs definitely change what’s possible. There’s a lot of enthusiasm in the field. It requires much less development to accomplish things, so that’s rewarding. It’s been a fast moving field for all 20 years, you constantly have to learn and change your business plans which I enjoy but isn’t for everyone.

        It’s been fairly rewarding financially – I took the startup path so not optimal earnings, but overall it’s a solid field of software. Socially, fine? I’m neither curing cancer nor maximizing cigarette sales. There’s something to be said for feeling like you’re part of something world changing. I worry some about whether AI will be a net negative impact on the world, but decided it was better not to leave the field to those without ethical concerns. When I meet other software folk there was usually a deference, like I was doing the “serious” work compared to them. I’m not terribly driven by status, but it’s an observation. It’s a big enough topic you can find companies actively doing evil and companies trying to change the world for the better easily enough.

        Two big downsides – I’ve seen so many dead businesses along the way. Partially it’s software, but the field finds lots of idealist founders and VC funding and lots of great software gets thrown out. Or a business makes it and then can’t adapt to the technological changes in the field and dies.

        The other is that your product is something trying to act intelligent but isn’t. It can feel bad when the system makes stupid mistakes in front of customers. If you have a type A – I’m going to work hard until I succeed personality it’s tough when the software just can’t learn what you want it to learn and there isn’t a way for you to just power through with smarts or efforts. You also need to pair careful analytical thinking with a comfort level about “I don’t really know what this is doing and why it sometimes fails and I’ve just got to try my best”. Its a somewhat uncommon pairing that causes a lot of people stress. Also “Let’s spend a lot of money training this model that we think will work but we don’t really know until we try and it’s going to take a month to find out” is stressful.

        Overall, I’m happy (hence sticking with it for 20 years). Not for everybody, but fundamentally an exciting field, and there’s opportunity to figure out how to use this technology across tons of different industries right now.

        1. Good stuff. Thanks for the feedback. The success rates of startups is quite low.

          Were you one of the lucky ones to find a startup that has continuously grown for 10-20 years? It’s rare to meet people who’ve been at one place for more than 5 years now.

          1. It is rare, isn’t it? Yep, about 18 years at one startup and then a couple years at an acquirer. We were bootstrapped, which was an extra challenge. I think we grew a little north of 10% a year, so didn’t explode but outlasted a lot of other businesses over the years.

        2. Buddhist Slacker

          It’s so funny that people think AI is some kind of new thing lol. AI has been doing evil for a long time lol.

          Meanwhile, chat GPT can’t answer my basic questions and it tells me to go research on my own lol.

  15. Hi Sam,
    Thanks for sharing your journey. I’ve been a fan of your blog for a year. I relate a lot to your stories since I’m also Asian and just hit 40. I was in telecom for 13 years, working big B2B sales up to being an Account Director. It’s a tight industry, hard to jump ship within. I retired early a couple of years ago, partly to be with my kid and partly out of job fatigue. After a year off, I realized I missed working, but I’m nervous about diving into a new industry and possibly losing all my telecom connections and experience. Any advice?
    By the way, my two cents on AI: It feels like a bubble. Right now, the winners seem to be the tool providers like Nvidia and AMD. Aside from OpenAI’s ChatGPT, I’m not seeing game-changers. If AI does revolutionize an industry, it’ll face human cost challenges, kind of like Uber’s taxi driver protests in Europe.

  16. This was a great post and super relevant to where I am right now. I left my job at age 31 (I’m now 36) not thinking I would retire but also without the need financially to work. In the last five years I’ve only volunteered or worked part-time in a field completely unrelated to the one I was working in (I was in healthcare, worked part-time on an organic farm). I’ve been toying with going back to work recently and I’ve applied to probably 50 different positions at healthcare startups that are looking to combine medicine with true wellness. And I’ve received 50 nos. I’m not deterred, the rejections actually make me laugh. It’s been interesting to find out just how much of a game it is to navigate your way into a new position. I have some friends that have offered to put me in contact with relevant companies, but I don’t know that I really want to go back to work for someone else, and until I do, I don’t want to use their connections. But I’m getting the itch to work again, and since I can’t land a job, I’m just going to have to create one for myself.

    1. Always good to create your own opportunity if nobody gives you one!

      I used to think 50 nos sounded like a lot. But now I think a lot starts at 200+. Everything has gotten more competitive, so we’ve got to apply to more jobs. It’s like applying to college and getting in. Acceptance rates are way down from 10 years ago.

      Good luck!

    2. Matthew Drybred

      Have you found out why you have been turned down? Maybe an answer to a question during the interview that the interviewer didn’t like?

      I had one opportunity that a recruiter contacted me about, so I went along with it, but then at the interview the hiring managers kept circling back to my reasons for working at 3 different jobs in 10 years. They wanted someone who would stay long-term, but then hired a recruiter to poach someone. *eye-roll*

  17. You have enough money to take an advisory role at an early stage startup. Friends of mine who have moved on to their second career and who have lower net worth than you have done just that — they’re no longer in it for the money. They get to work in an interesting role at a promising startup that can use their services but who don’t have the top tier VC money to pay top dollar for the best candidates. I think you’d have more fun approaching it that way. If you’re still bent on getting into a top tier funded startup, good luck.

  18. Matthew Drybred

    To me, there was nothing that made the world feel larger than when I was jobless and looking.

    While $250k a year sounds amazing to me in my market, I realize it doesn’t go that far in SF, plus kids.

    As others have mentioned, why not try teaching? You’re already doing it here.

    1. Hi Matt,

      I taught by coaching high school varsity tennis for three years. It was a good experience and very rewarding.

      There’s 6-12 months worth of credential gathering to be a subject teacher in SF. If we move to Honolulu, then I will consider it.

      How long were you jobless and what did you end up finding?


      1. Matthew Drybred

        Hi Sam,

        I’m happy that you have looked into it.

        Two 3 month stints between ‘08-‘09 and a 4 month stint in 2018.

        In ‘09 I found a bridge drafting position with a steel fabricator. I was there 5.5 years.

        In 2015 I went back into the automotive industry as a service advisor. I had $220k-$250k a month in sales and made excellent money, but in 2018 my commission was cut 70% by the owner despite my manager’s objections.

        So I spent 3 agonizing months searching, ended up with 3 offers, and chose a small hydraulic component distributor and system manufacturer that I hoped I could help to grow. But they didn’t want to grow, so now I design wastewater treatment equipment using SolidWorks.

        1. Glad you found something steady. 3 job offers is great in comparison to my none :)

          There are two schools I’d like my kids to attend in Honolulu if we move. I’m certain I’d love to be a teacher at their HS for the last 4 years they live with us. I will miss them dearly.

          1. Matthew Drybred

            Thank you.

            In my market there are/were plenty of jobs paying ~$50k -$60k a year at the time, and since I was well on my way to FI, I could afford to set realistic expectations and see if I could find a niche where I could help a company to grow.

            It also took a solid 60 days to gain any traction in the job market because many listings are stale.

            That sounds like a great idea and might even lead to some comedic opportunities when your kids hit their teen years.

            Have you thought about a YouTube channel, or do you think that would negatively affect this product?

          2. Matthew Drybred

            Thank you.

            In my market there are/were plenty of jobs paying ~$50k -$60k a year at the time, and since I was well on my way to FI, I could afford to set realistic expectations and see if I could find a niche where I could help a company to grow.

            It also took a solid 60 days to gain any traction in the job market because many listings are stale.

            That sounds like a great idea and might even lead to some comedic opportunities when your kids hit their teen years.

            Have you thought about a YouTube channel, or do you think that would negatively affect this product?

  19. Thank you for your honesty. As a California teacher I have had opportunities to retire since I was 55 year old. I was very tempted especially when a physical and mental health crisis nearly institutionalized me 5 years ago. I had to build a village around me to climb out of the black cave of desperation. The first step was TELLING THE TRUTH. I talked to trusted workmates; I returned to a counselor; I found an amazing physical therapist; I told my closest friends and family members that I was struggling and desperate; and then I was referred and reluctantly accepted psychiatric help. I started keeping a budget to realistically assess my options in case retirement would be the ultimate path I took.

    I am writing all this because it took all those steps to realize that I had more options than just retiring. I jumped from middle school to high school which worked different teaching muscles. I loved it. My village helped me to look at my job in a different way, list the factors that were causes the most burnout. I change my work life to minimize the burnout and maximize the wonderful benefits of living a life of service. I became less about achieving “curriculum standards” and more about teaching crucial teambuilding and critical thinking skills. This became a saving grace for many of my students during the pandemic. I am now ready to retire after the best teaching year of my life. I am filled everyday with fun, learning, grace and mercy. I call this year my “victory lap.”

    Financially, all the steps I begrudgingly took proved critical in securing a comfortable life for myself. At 55, I would have retired with a pension worth 45% of my salary at that time. Today I will retire at 70 % of my highest year of income which is 40% of what it was back then; full medical until my husband and I get to Medicare; my son is in his last year at University of Michigan with no student debt, and I have tripled my 403 b.

    If you are considering early retirement because you are lost emotionally, physically, or spiritually, cast a wide net for a solution. Chances are good that you will find an alternate solution if you are honest, open minded and willing.

    1. Wow! What an inspiring story, Mary Ann! I am fifty, work in tech, and feel very burned out. I dream of quitting my job every day. But you’re confirming what I have suspected for a while– there are ways to keep one’s income and occupation, while managing burnout. Throwing in the towel sounds glamorous but comes with its own issues that surface in the longer term. Thank you for sharing an alternate point of view.

  20. Sam – I am really perplexed by your post, and some of your other recent posts alluding to you going back to work. Are you for REAL? Is this some elaborate joke on your readers?

    Are you REALLY looking for a job??? Why? I mean you have tons of diversified passive income, my guess is you have a ~$10MM net worth, you have built a successful website with interesting content, you are a talented writer. Why the hell would you waste your life now working for somebody else? And in the latest bullshit craze about “AI”, out of all the options out there?

    I am genuinely puzzled, I do not mean this in any disparaging way.

    I also retired 11 years ago at 34, and never spent a day regretting / wishing I could go back to finance / the daily grind.

    I just don’t get it, sorry.


    1. Crazy right? It costs me no money to look and try, only time. And I’m genuinely curious about AI and the possibility of riding the rocketship with a great group of folks again. I miss being a part of a team. It’s fun.

      I can only write and play pickleball and tennis so much. But as we chatted in an e-mail, I don’t have the freedom to go sailing for 6 months like you. With kids, I have to stay grounded for the next 15 years. So I might as well do something interesting once they go to school full-time.

  21. I’m trying to reconcile how you are going to make a $500k speculative investment in AI, but you are somehow worried about paying for college for two kids?? Why? You’re good, man.

    1. Means to an end. 3 years to build a $500,000 position and multiple private funds.

      College tuition really could be $750,000 over four years in 15 years. And I’ve got two kids.

      So I’ve got to figure out how to invest my capital wisely to be able to comfortably pay these outrageous prices. I highly doubt they’ll get scholarships.

      Are you investing in AI? How are you planning to pay for college?

      1. Only investing in AI through low cost MFs or index funds. 529s for college for two kids. If in 15 years private college costs 750k or more, it will have become a luxury good so out of reach for the masses it will take on a different meaning all together. It may be see as the new “grand tour”. A 4 year vacation for the privileged. The workplace may view it as neutral or even a negative as opposed to time spent actually working. Idk but higher ed will change significantly very. We’ll see how it shakes out.

        1. Not sure why this wouldn’t be an option or even the preferred method. I went from community college to U of Illinois (#12 public university), then full ride for graduate school at Illinois. Transferring is common and advantageous for determined students. A classmate transferred to Yale during grad school after starting at a CC.

          1. One is at state school out of state (but gets in state tuition), one at private in Boston, and one more to go – expect likely private

              1. I’ve been lucky with my career and 529s have performed. I’ve been paying from yearly cash flow and hope to use the 529 to fund next generation.

                What we do for our kids right?

  22. I left my last traditional job in 2020 and have been doing contract consulting assignments on a remote basis since then. I’ve still pursued some traditional jobs and gotten a few decent offers (although nowhere near the total comp I made at my peak from 2010-2015). I turned those jobs down because I just couldn’t bring myself to commit to the grind. With contract work, most of my assignments run 4-6 months. If I get sick of the work or the company, I know there’s a light at the end of the tunnel. And I do sometimes get sick of them. I’ll often take a couple months off before pursuing a new assignment. This has worked out great for me, but after 3 years of doing it and reaching my mid 50s, I’m starting to feel that my marketability for traditional jobs has faded. In addition, my specialty is SEC financial reporting (10-Ks, 10-Qs, proxy statements, etc.) and thanks to current economic conditions and anemic IPO market, the demand for my services has fallen off the table this year. My last assignment became very part-time during the summer, and now that I’m interested in a new assignment, I’m not seeing anything worthwhile. So I agree with Sam’s point about staying somewhat connected to the job market via consulting, but know that there are risks involved.

      1. “The closer the end, the easier it is to start!”

        Exactly this. Over time, I have learned that I can put up with just about any form of corporate BS for 3-6 months. But 3-6 years? Not so much. A few of my consulting clients approached me about permanent positions, but I told them thanks but no thanks. I had already seen too much.

  23. Sam:

    Do you miss being part of an organization, the challenge? I’m assuming the drive isn’t the money or benefits, bc you can buy those. You’re not “too old” to get your PhD and then teach. That would have a lot of benefits: status, challenge, opportunity to work at a college and perhaps discount/free tuition for your kids. Colleges have great job fairs and recruiting centers. You could also consider doing something with computational finance (MS( combining AI/ML. Thanks for the excellent posts and advice!

  24. My suggestion is a bit out there but perhaps folks should consider un-retiring by taking a job in the public sector. Lots of folks in the military who retire with a full pension then go into a government position. They are used to folks coming in “late in life”. Government hiring is highly regulated to prevent ageism and other forms of discrimination. Federally, the expectations can be pretty low and you can apply for telework, alternative work arrangements (e.g., 4/10s or 9/80s) and the vacation time, paid holidays, and benefits are excellent. Plus you get annual step increases + COLAs and access to contribute to the TSP. With unemployment still below 4% they are starved for talent. There’re are lots of positions where there’s no overtime. 8-4:30 M-F is like a part-time job when you’ve been grinding for years. Is it earth-shattering work like AI? Not a chance. But if you’re middle-aged and looking for something to do to keep busy that pays decently and have a reasonable work-life balance, you could do far worse.

    1. OK, good suggestion. Will check it out! Although, I might be extremely frustrated with the inefficiencies.

      “Is it earth-shattering work like AI? Not a chance” Nothing is really that earth-shattering. But creating something out of nothing comes closest.

      1. Buddhist Slacker

        We’re hiring lol. you’ll find state local and county jobs on there.

    2. Sorry, run!!!! It’s a common fallacy what you’ve listed because it was true about 20 years ago. I work for state government. It’s a hot mess right now. The pay is well below the private sector after years of frozen raises due to one budget crisis or another. We can’t attract talent and everything (especially the mentality) is NOT flexible. Over the years the benefits have been cut and cut (My maternity leave was 4 weeks paid at 70% and 2 weeks unpaid for example. Public pension COLA is capped at 3% which is awesome when inflation is at 9%. I could go on.). The schedules are not negotiable and there is a huge push to fully in person. Plus, everyone and everything feels so OLD. A friend of mine started as a college intern at 21 and happened to stay. He was the youngest person in the room then. Today, at 41 he is still the youngest person in the room and he’s in IT. All levels in the public sector have spent years sopping up the excess Baby Boomers from the economy cheaply and so not having to worry about being an attractive employer. They cannot wrap their minds around the demographic change. They are too used to using public sector employees as “lazy” punching bags. In my experience, people who were in the private sector without strong public sector experience quit in under 18 months, unless they are over 55, in which case they are super grateful for the job and the dated environment and resistance to change just feels cozy.

  25. I’m in the same boat of consulting part-time, but have done it consistently for 16 years now, since leaving the traditional corporate job. The bulk of my work is as a recruiter, so I offer this word of warning, having hired thousands of people in 25+ years of recruiting: Even if you have a steady stream of consulting work on your resume, prospective employers don’t value it as much as the traditional, in-house work b/c too many job seekers say they’re consulting when they’re in-between jobs but the consulting projects aren’t very substantive or are few and far between.

    1. “Even if you have a steady stream of consulting work on your resume, prospective employers don’t value it as much as the traditional, in-house work b/c too many job seekers say they’re consulting when they’re in-between jobs but the consulting projects aren’t very substantive or are few and far between.”

      Wise advice! Any inside tips you can provide me and others looking for a FT job after years of no traditional work?

  26. I’ve been out of the tech industry for about 5+ years, and I can relate to how quickly both your network connections and latest technology knowledge fade. Being an ‘average’ investor, without deep knowledge of AI, I’m tempted to just stay put with low cost index funds and let the indexes benefit or not from the AI promise — they have certainly boosted the indexes earlier this year. I find it interesting you want to ‘overweight’ AI given your relatively conservative asset allocation.

  27. Why do you want to go back to work? You have enough assets and passive income to live better than most people in the United States. Even if you convince yourself that you need another house or two, you really don’t. You can do whatever you want at this point. Why get a job?

    If anything, start your own business and do something interesting. It doesn’t have to be a web business. Start a food truck or a kids camp. It doesn’t matter.

    Working at some AI startup may be a way to make more money, but the returns are diminishing. To get one of those $250k jobs at a start up will take up a massive amount of your time and mental capacity. Why do it? Is it just for the challenge? Just for the extra money? Are you bored?

    Honestly, I think it’s time to move out of SF. Go to Hawaii. You’ve been talking about it for years. At 45, the time is now. Sell your homes in SF and find your little beach place in Hawaii. Then go enjoy life there. Get a job at a resort or something if you’re bored when you get there.

    Life’s too short to get into the mess of SF start ups now. You have money. Plenty of it. Time is what you’re running out of.


      1. The reason they stay in SF I am guessing is for the kids education. Asians take education seriously and want their kids have the best education possible.

    1. Not sure what else I can say about the why beyond what I’ve written in this post. Are none of the reasons I’ve listed not valid to you?

      It’s definitely not about buying another house or two. Don’t think I mentioned that.

      What is it that you do? And if you are retired, how long have you been retired and what do you do with your free time? thanks

  28. It’s so crazy to me how much the job application process has changed since I graduated from college.

    I feel technology has made the process so much worse for applicants. For so many companies and jobs, it’s too “easy” for anyone to apply from anywhere so hundreds or even thousands of resumes are submitted for one role. And because of that many qualified individuals are tossed out because of algorithms within seconds when they really deserve to be put in front of human eyes.

    But the ways of the past are behind us and we have to find ways to adapt. It will be a very anxious time for me as a parent when my kids grow up and need to apply to colleges and jobs.

    Striving for the best but having low expectations, fishing in a lot of pools, networking, staying patient, and embracing resilience will be crucial.

    1. I work at a successful and growing publicly traded tech company. We don’t employ any algorithms for screening job applications. I typically set aside about 15 minutes a day to review all applications for positions (typically analyst or technical product management positions) for which I’m the hiring manager (HR is not really involved in vetting applications). All managers are expected to do the same. It takes me 5 seconds to tell from a resume if someone is totally unqualified (which 80%+ of usually are) and in my experience HR is very bad at judging candidate quality (understandably, they don’t know the minutiae of the job). I find it hard to believe that algorithms are being heavily used to filter job applications for non-entry level professional jobs. Maybe I’m naive/ignorant.

      1. Yours is a good way of doing things. Alas at big companies, HR wants to “provide value” to busy hiring managers, so they insists on doing the first cut, often with a (ranking?) algo. I always ask them nicely to “leave a CV in if they are unsure”. Only once did I have an HR person interested enough in the hiring manager’s point of view that we scheduled 15 min to review what I would shortlist vs not. It’s a volume business for them unfortunately.

        1. Matthew Drybred

          I work with SolidWorks and MicroStation and hiring HR reps were turning down my applications for AutoCAD drafting positions because my CV didn’t have “AutoCAD” on it.

          This would be like turning down someone with Mac experience instead of MS.

          1. Buddhist Slacker

            Oh yeah it’s all about the keywords. Sam you should know all about SEO and gaming the keywords so do that with your resume obviously and of course post your resume on all the sites, with LinkedIn being most important I think. Algorithms are the most basic form of AI lol. I still get random emails from recruiters. I haven’t updated my resume in forever. I should update it with my new healthcare experience and see what comes up just for fun.

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