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.

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!

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.

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!

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. I figure 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. 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, 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 “saveten” to save $10 at checkout.

Join 60,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. 

About Author