When You Can Afford To Retire But Are Afraid To Quit Your Job

My FIRE challenge right now is actually the RE part. We are absolutely in a financial place to officially retire (my husband already is), but I’m holding on due to, well, fear. I have a very good job with excellent benefits working with great people that isn’t hard but doesn’t fulfill me at all. Quitting would put strain on some of those great coworkers so I’m battling with that guilt as well. I’m struggling with giving up the safety of corporate life. 

— Sarah

I hear you and feel you, Sarah, as I consider myself quite risk averse. Scott and I did the RE (retire early) part in reverse compared to you and your husband. I left the corporate grind in my mid-30’s to start a business, which had a flexible schedule and was largely location independent from the start. Almost 10 years later, Scott finally left his desk job, when we were both mid-40’s.

It took me several years to convince him, and it had taken me several years to convince myself. Here were three strategies I used:

Fight fear with fear

I still consider myself more fearful than the average about a lot of things, but my workaround for fear of RE was to replace it with bigger fears. There are actually quite a few!

1 – FOMO, or Fear Of Missing Out on what early retirement could bring

Sure, leaving a job means missing out on a steady paycheck and health benefits – very important things – but in both our cases, we had busy management jobs where it was next to impossible to take any meaningful time off. The key item on our wish list was travel – we have a long list of travel destinations to hit – and we both believe that travel experiences make life more meaningful. So FOMO in this case wasn’t just chasing a fad that some social media influencer was peddling, but something meaningful to us. When we got scared about leaving our jobs, we scared ourselves in the other direction with the lure of travel.

2 – FOMO, Part 2, or Fear Of Missed Opportunities

While leaving my job meant less steady money, it also meant unlimited upside. I didn’t have big dollar targets, but I do like to be fairly compensated, and human resources (my area of expertise) isn’t a big money draw compared to other functions within a typical company. For me to maximize my earning potential, working for myself as a consultant was definitely the more lucrative career path. So, whenever I felt the fear of being unemployed and penniless coming on, I fought it with the fear of selling myself short.

3 – Fear of regret

What if we didn’t give the FIRE lifestyle a try and then something happened to one or both of us – would we have wished we worked more or at least gave FIRE a try? What if we didn’t start our travels and suddenly we couldn’t (this fear was pre-pandemic, and no, I didn’t have any premonitions about 2020) – how much would we regret not getting started? What if we got to the end of our life with extra money – would we have wanted to spend more of it?

Solve for the biggest pain point

There are a lot of what-if’s when it comes to early retirement, and figuring out the scariest ones is another way to coax yourself into early retirement. My biggest what-if was the availability of health insurance. Working out the insurance bit gave me a lot of comfort that we could handle the rest.

• What if we can’t afford the insurance premium? I put a buffer into our budget to cover it. It’s also part of the allure of Costa Rica for us.
• What if the Affordable Care Act goes away, and there is no insurance market? One of us could look into Barista FIRE, or getting a job for the health benefits. Again, there’s Costa Rica!
• What if we encounter a medical emergency and need expensive, difficult specialty care? While I’d love to have a Cadillac insurance plan from a generous employer (and Scott was walking away from one of those), if this were a true medical crisis, I would also want the time and mental bandwidth that a FIRE lifestyle brings.

You can play the what-if game all day long, and either scare yourself out of early retirement or realize that most of the problems are solvable if you think long enough about them.

Use motivational quotes when your own motivation is flagging

I love quotes. I keep a Word document that is now almost 50 pages long, where I copy quotes that I encounter as I read. When I am second-guessing myself, I have a few go-to motivational quotes, especially about the value of time:

The money we receive in return for our eight hours of work each day can be spent any number of ways; the only thing we cannot buy is extra time.  So, during the minutes we have, I believe it is better to live a dream rather than to simply dream it.  The dream is the start of something greater, something that impels us to make daring decisions.  And it’s true that the person who pursues a dream takes many risks.  But the person who does not runs risks that are even greater. 

—  Paulo Coelho

The Coelho quote is my all-time favorite. I get recommitted to my goals every time I read it.

You know, some people say life is short and that you could get hit by a bus at any moment and that you have to live each day like it’s your last. Bullshit. Life is long. You’re probably not gonna get hit by a bus. And you’re gonna have to live with the choices you make for the next fifty years.”

— Chris Rock

Chris Rock is one of my favorite comedians (I tried to find the set with the above quote about long lives, but instead found this funny bit about long relationships). While this quote might read like a warning against early retirement, I look at it as a reminder that life is long and can seem even longer if you’re not doing what you want to do.

It’s never too late to become who you want to be. I hope you live a life that you’re proud of, and if you find that you’re not, I hope you have the strength to start over. 

— F. Scott Fitzgerald

I love this reminder that you can always start over. If you retire and realize you did it too early, you can go back. If you stay for one more year and find yourself wistfully wishing you picked the RE option, choose RE now (just give some reasonable notice to your employers!).

The first step is the hardest

Sarah mentioned that she feels a bit guilty about leaving her team short-handed.

Scott found himself in a similar situation when he left his job. He didn’t want to leave a standard amount of notice, which would leave his team in a lurch and scrambling to cover his role.

He decided to give them a lot of notice, in fact it was almost a full year. The hardest step was the first one – telling his company he was planning to leave. Once that was done, and his company was supportive in his decision, that paved the way for a thorough and successful transition plan.

It was truly win-win. We were able to continue receiving his corporate pay and benefits for an extended additional time, but knew it would end sooner than later (and we could start making travel plans for the future!), and the company had the benefit of time to consider how to fill his position, and put that plan into action, with Scott helping out in the process.

If they weren’t supportive of his leaving and helping with a transition, we were prepared for him to leave his job soon after providing the notice. But if that happened, Scott would have felt clear in his conscience that he made his best attempt to ensure his team would be on solid footing when he left.

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Once we did start the FIRE lifestyle, I heard from multiple friends about how inspirational it was to them that we had taken the leap. We talked about it, we did it and we gave them ideas for how to think differently.

I hadn’t realized that our FIRE journey would impact other people in this positive way, but it did – and perhaps Sarah’s team might feel that same benefit.