After 12 years of FIRE (financial independence retire early), I went back to work. Unfortunately, I only lasted four months. Here’s my story of what went wrong. I purposefully waited months to release this post to ensure I was thinking logically and not emotionally.
From the end of November 2023 through March 2024, I re-entered the workforce. Having worked 11 years at my last full-time job from 2001-2012, I was disappointed I couldn’t even last a year.
When I decide on something, I always try to give it my best before moving on. However, after four months, I decided I had enough.
This post is a journey of self-discovery about the difficulties of going back to work after a long time off. It also provides insights into how age and wealth change your tolerance for work. Hint: it declines.
Working for a company is like a marriage. You date through multiple interviews, and both sides take a leap of faith if they see potential. However, like many relationships, they don’t always work out.
The silver lining of having a short stint at work is that I now better understand what I want to do next time. Additionally, I know that I can return to work for a decent salary if I choose to. It can be difficult finding a good job after retiring for years.
Background On Why I Went Back To Work
I had been seriously considering going back to work since April 2023, when I penned my post, “Sadly Giving Up On Retirement By Going Back To Work.” After experiencing work freedom since 2012, when I left my day job in finance, I was looking ahead to the future.
At the time, many readers thought I was joking, but I was serious. I had calculated the cost of college in 2036 and decided I should probably start generating some extra income to afford such an enormous future expense. We’re talking around $450,000 for four years of public college and $750,000 for four years of private college by then, and I have two children.
I read a lot of research about the affirmative action Supreme Court case that seemed to demand higher academic excellence, extracurricular activities, and even personalities for Asian applicants. There were countless examples of Asian kids with excellent grades, test scores, and activities getting rejected from top colleges. As a result, I concluded it was probably best for me to earn more money for my kids, given they are unlikely to get any grants or scholarship, even if they excel.
I half-heartedly looked around that spring and summer but didn’t find anything interesting, so I shelved the idea until November 2023. That was one month after we bought an ideal house for our family. Suddenly, the need for more money shot through the roof!
Actions always have consequences. Instead of complaining, I forced myself to look for a work opportunity through my network.
The Job Opportunity
I was feeling the financial strain of having less passive income and an empty previous house that wasn’t generating any rent. So, as any rational person would do, I decided to look for active income opportunities. I sent a feeler out in my newsletter, and a long-time reader and ex-colleague reached out and introduced me to a fintech startup in San Francisco.
I met the team, thought they were great, and received a good offer for roughly 20 hours a week of work. Even though I was part-time, I was given a founding role as the head of content at this startup, along with equity. I was grateful for the opportunity and their flexibility.
My goal was to last a year until November 2024 and renegotiate for a full-time role because I hoped to love the work. By then, my daughter will also be in school full-time, meaning I will have more time.
I imagined weaving this company’s product into my writing on Financial Samurai, given the synergies. The work was remote, but the founders were in the office around three times a week, so I went in once a week for the first month.
Why I Could Only Last Four Months In My Part-Time Consulting Role
Out of respect for the company, I won’t mention the name or the people. This post is not about criticizing them as they are good people. Instead, this post is intended to help those who are thinking about going back to work, or shifting to consulting work, make better employment decisions.
After all, many people who FIRE tend to eventually have an itch to return to work in some capacity. Maybe they’re bored and are looking for camaraderie. Or perhaps their net worth took a hit after a bear market.
Additionally, this post will highlight some of my personal flaws in hopes I can improve. Overall, 70% of the reason why I failed to last longer than four months was due to me, and 30% due to the company. Here are the reasons why my work stint was so short:
1) Part-time Consultant at a Seed-Stage Startup Is Not A Great Fit
When you’re at a seed-stage startup that hasn’t launched its product yet, the work is endless. After about a month, even though I delivered on all my requirements, it didn’t seem fair to the team that I was part-time. The company deserved someone full-time.
Because I felt this way, I ended up working almost every day of the week instead of on our agreed-upon Monday, Wednesday, and Friday schedule. There was always so much to do. The 20 hours a week we agreed upon quickly grew to at least 25-30 hours a week.
Over time, the emails, Slack messages, video meetings, and interviews on my off days began to wear on me, as they interfered with my time with my daughter.
Too much interference with personal time
For example, one Tuesday (off day), I took my daughter swimming for a regular 3-hour outing. But because I had agreed to a meeting that afternoon, I had to cut our swim session short. Instead of having a sit-down meal at In-N-Out Burger afterward like we normally do, I decided to go through the drive-through to save time. However, the line took forever, and I started feeling highly agitated given I didn’t want to be late.
What was supposed to be a relaxing day with Daddy turned into an anxiety-filled one instead. I’m not one to ignore messages. If something needs to be done, I will do it, even if I’m supposed to be off. But because I’ve been used to being a full-time father for 7+ years, if something hurts the quality time I have with my children, I probably get much more agitated than the average dad.
You can be a part-time consultant for an early-stage startup, but you might not last long either. During my four months, two other contractors left. But it seemed like they had a set work duration or work goal. Early-stage startups are looking to save money and be as scrappy as possible. However, the equity reward I was given wasn’t enough to motivate me to consistently work beyond expectations.
2) Difficult to Work With So Many Meetings and Slack Messages
Before joining this startup, I never used Slack. In fact, one of my quirks is that I keep my iPhone on sleep mode almost the entire day so I’m never hardly bothered. My WhatsApp and messages don’t alert me when new notifications come in either. I check my messages when I’m free, and that’s the way I’ve liked to do things since 2015.
I’ve developed this habit because I require no distractions in order to write. The need for peace is why I’m often writing between 4 am – 7:30 am and after 10 pm. These are the times when the house is quiet.
Unfortunately, my Slack messages were constantly going off. I tried putting them on silent, but then I’d miss some notifications from the CEO. After missing an event because I hadn’t responded for over two hours, I turned on my notifications, which then hurt my productivity.
In addition, I’m not used to being in meetings. As a result, I find meetings that last longer than 15-30 minutes to be unproductive. However, the reality is, meetings need to happen to get everybody on the same page to get things done. Hence, it’s my bad for not having better meeting endurance.
The thing is, if I’m in meetings or on Slack, I’m not writing. And my job was to write and edit pertinent content for the product. I’m not as bad as Jack Nicholson in the movie The Shining. However, I can empathize with his annoyance in this classic movie scene below!
3) Lost My Voice And Personality As A Writer
I write because I enjoy the process. It’s fun to write freely in my unique style. However, my personality was stifled by the CEO’s heavy editing. I understood what they wanted but could never quite replicate their desired voice, even after 20 articles. My writing was either too complicated or “sophisticated,” or not “cool uncle” enough. After a couple of months, the constant heavy editing after my pieces were already edited was demoralizing.
After a couple of months, I could tell the first-time CEO, was getting frustrated too. So, I asked my wife to try writing the articles in the CEO’s desired voice, with me reviewing and editing her work. This approach worked better, and I felt we had a good solution for dividing and conquering different types of topics between us.
However, my joy for writing slowly began to fade. I didn’t have control of the editorial calendar as expected, which would always change despite agreeing on the schedule the week before. It felt jolting to pivot so much last minute.
Didn’t want to provide the same feedback like I was getting
In one instance, the CEO wrote a personal article that needed more structure and action points. However, I dared not make more than a few suggestions, fearing I might offend them. So, I basically said the article was great as is, with suggestions for creating some subtitles for easier readability.
My hope was that by empowering the CEO with minimal suggestions for change, they would notice the large difference in editing styles and also empower me with my work. Unfortunately, my articles still ended up getting 50-100 edits each, which became comical at times. There was simply too much nitpicking that didn’t matter.
Funny enough, a couple of the sections in articles we published, written by the CEO, were questioned and criticized by another employee. The employee thought I had written those words. This shows how subjective writing can be; five people can read the same article and come away with five different opinions.
This example also highlights the power dynamic at play, where employees are fearful of criticizing those in power but not the other way around. I had largely forgotten about this power dynamic since it has been so long since I had a boss.
4) I Got Managed Way Too Much
If you haven’t had a boss in a while or are financially independent, you might have a lower threshold for taking orders than in the past. I fully admit my threshold for being told what to do has declined since my 20s and 30s.
The CEO and I had a video meeting once a week and often two catch-ups throughout the week. This isn’t a lot in the grand scheme of things. And perhaps most employees would find all this face time with the CEO flattering. However, I preferred fewer meetings and mainly wanted to execute the game plan for the week. Again, if I’m in meetings, I’m not writing.
With a plethora of things for the CEO to do, I felt bad each instance they had to spend time giving me guidance after the first couple of months. Instead, I hoped they would just let go and trust my experience and expertise. This was my expectation to run content, when I first signed on. But it never quite happened.
Understandably, the CEO of the startup wanted their imprint on everything I produced. However, I also believe a good CEO knows how to trust their employees and delegate.
5) Started Noticing My Colleagues Were Too Busy To Care
Like most people, I appreciate praise for a job well done. While working in finance for 13 years, I used to keep a subfolder in Outlook of nice e-mails. The hours were so long that it felt good to revisit kind words from bosses or colleagues on occasion.
Unfortunately, it seemed as if only about one out of every three articles I wrote was read by my small team of colleagues. One senior employee might have read only one out of every 10 articles I wrote. This was even after I was encouraged by the CEO to highlight the posts in Slack. Being ignored never feels great.
Even after I asked my colleagues to listen to and rate a relevant podcast that would help the company, none of them did. Leaving a review costs nothing and requires less than a minute of time.
When you start sensing your coworkers don’t care about your work, especially when the team is small, you can’t help but stop caring about their work and the overall product too. There’s a reason why they hang “Employee of the Month” plaques at McDonald’s!
6) The Criticism That Broke the Camel’s Back
Almost four months in, I was actually feeling pretty good about everything. I had dialed down my sensitivity towards the heavy editing of my writing and the indifference by my colleagues. I recruited my wife to help out with the writing and editing of some articles, which felt great as I’ve been wanting her to get back into the workflow. It also felt like the CEO was giving me more leeway to control the editorial calendar.
As head of content, I also launched their weekly newsletter. I thought I was doing a good job given the high click-through rates. Like all my articles, the CEO reviewed and edited all my newsletters. No problem. We had a good system going.
Then, one afternoon, I got a stern Slack message from the CEO saying something like, “You didn’t include the proper links to the articles. Be more careful next time as I expect you to have the newsletter ready to publish when I review it.”
Unfortunately, that was the message that broke the camel’s back because I thought we were supposed to be a team. The CEO had been heavily editing and revising all my work since the beginning, always changing the final copy of the newsletter as they saw fit. So why were they suddenly going from a collaborator to a criticizer? I responded with a, “Will do.”
An editor is supposed to help check everything and make the final product better. I went from feeling like we were a good team, to feeling like a failed soldier, despite getting the newsletter off the ground in the first place.
Deciding to Make a Change
Maybe the CEO was having a particularly stressful day. Or maybe I’m too sensitive. I decided to sleep on my displeasure to see how I’d feel the next day. And the next day, a Tuesday, I sent the CEO the message, “Hi X, this isn’t working out.”
They wanted to talk that day, my day off with my daughter, but I told the them let’s chat the next day when I’m back on. Then on Wednesday, the CEO decided Thursday would be my last day.
I wasn’t surprised, but I thought they might have wanted me to finish my responsibilities for the two-week sprint we decided on that Monday. Or perhaps, they would have proposed a different working arrangement so both sides could benefit. We were only a month or so away from launch. But instead, it was sayonara.
The departure felt impersonal and sudden. During the exit call, any warmth the CEO used to have disappeared. What an unceremonious ending to what could have been a great long-term partnership.
Would Have Lasted Longer At Work If I Had More Free Time
If I were in my 20s, I would have sucked it up and kept working for at least a year. I remember being great at smiling at my bosses while gritting my teeth. I also would have come to the office once or twice a week to develop stronger relationships, even though I couldn’t write if I was talking or in meetings.
But something disrespectful happened, which made me decide to stop going in weekly after a month. Now that I think deeper, this disrespectful event permanently changed my enthusiasm for consulting with the company. I’ll share the story in an upcoming article if you’re interested.
If I had started this part-time consulting opportunity after September 2024, when my daughter starts school full-time, I believe with an 80% probability I would have lasted at least a year. But with too much work bleeding into my off days, I had to quit. I needed to cherish these final days at home with my daughter.
The below quote and video encapsulates my remaining time as a father well.
Parental Guilt Can Be Overwhelming
Through this work experience, I’ve realized I have more dad guilt about being away from my kids than I thought. I assumed it would be easy to work again since I have stayed home with my daughter since she was born in December 2019. Instead, it’s precisely because I’ve spent so much time with her that I feel so bad not spending time with her when I can!
I experienced this dad guilt again when fellow dads planned a trip to Mexico for four nights and four days. I thought I’d be thrilled to go drink tequila, play golf, and go deep-sea fishing without my family. But I have a difficult time choosing to spend time with anybody else besides family for that long, given we’re always together.
Deciding to work for money over spending time with your children while young is tough! My colleagues have to be amazing, and the work has to be super important for me to continuously make that trade-off. Alas, as an older parent, you are more sensitive to the tradeoff.
Money Matters For How Much You’re Willing To Work
I went back to work partly because I’m on a journey back to financial freedom. My choice to buy a house I didn’t need necessitates a rebuilding of my passive investment income.
But I also want to be part of a great work team again once both of my kids go to school full-time. I used to love battling for business together with colleagues, growing in my role, and going to happy hour after… or so I thought. Then my financial situation improved.
On February 1, 2024, I found tenants for my old house. That provided a lot of relief after the house sat empty for almost four months.
Then I received a surprise real estate capital distribution of $106,000 on April 11, 2024. It gave me more confidence to speak up about my suboptimal work situation.
Meanwhile, there were crazy bidding wars for single-family homes on the west side of San Francisco, where I own property. As a result, I felt wealthier. Finally, the stock market continued to do well.
All of these positive financial events made me question why I was spending 20+ hours a week consulting when I could be spending more time with my family and enjoying life. But even in a bear market, I’d question spending time working for money when my investments would easily lose 5-10X the amount I’d earn in a year.
Takes Effort To Find The Best Work Fit
I still would have liked to continue earning my consulting income if the work arrangement was awesome. But it was not, so I chose happiness and freedom over money. I can do so because I have diligently saved and invested most of my income since 1999.
Instead of consulting for a seed-stage startup, I’m better suited to consult at a Series B or later stage startup. These startups have usually been around for 5+ years and have more infrastructure in place. The CEOs also have more experience managing a team.
I wish the startup that hired me the best. I appreciate the opportunity they gave me. I’m just sorry things didn’t work out for both sides. But I’m glad I went through this experience because I now know better what to look for.
Summary of Going Back to Work and Failing to Last
- Don’t be too proud to go back to work in any capacity to provide for your family. It is your duty and an honor to protect them.
- Expect constant meetings, management feedback, and changes in responsibility. Work is work, not play, no matter how hard a company tries to make it fun.
- Not feeling heard or appreciated by your colleagues is hard. But remind yourself that as long as you are getting fairly paid, try not to feel disappointed in others’ lack of appreciation for your work.
- The more you love or need money, the easier it will be to take criticism and choose work over spending time with your children and vice versa.
- Suggest a different arrangement in terms of work hours, pay, and responsibilities if you want to stay.
- Finding the right company at the right stage of its maturity is extremely important for fit and longevity. Working at a startup is not for everyone.
- If you just can’t make things work after trying, it’s best for both sides if you move on. Don’t settle for a suboptimal situation if you’re going to spend so much time working.
As for what’s next, here’s my plan: Instead of looking for work again before my daughter goes to school full-time, I’m going to wait until after she starts and then make a decision. This way, I’ll get a better idea of my free time.
Have you ever had difficulty adjusting to a new company? If so, how did you manage to adapt? What’s the shortest amount of time you’ve worked for a company? How can we do a better job of determining whether a new work opportunity is the right fit to reduce wasting time and energy?
Recommendation For Those Who Want To Quit Their Jobs
Hate your job? Pick up a copy of “How To Engineer Your Layoff” that teaches you how to break free with money in your pocket. Both my wife and I negotiated severance packages, which enabled us to live the lives we truly wanted. My book has been updated six times since 2012 with new information and strategies. Use the code “saveten” to save $10 at checkout.
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I Went Back To Work And Only Lasted Four Months is a Financial Samurai original post. All rights reserved.
