If I Could Retire All Over Again These Are The Things I’d Do Differently

If I Could Retire All Over Again These Are The Things I'd Do Differently

I can’t believe I’ve been writing about early retirement since 2009. The first three years of Financial Samurai was me mainly trying to figure out how to retire early. The subsequent years has been me touching upon various aspects of post-retirement life.

For the most part, early retirement has been everything I hoped for. Freedom is priceless. But I’ve also highlighted a lot of negatives that I could not have expected until living as an early retiree for several years.

We can pontificate all we want about what it’s like to do something or be in a particular scenario. But until you experience it for yourself, there’s no amount of planning that can prepare you for some of life’s big moments.

Now that I’m deep into early retirement, I’d like to share what I’d do differently if I could rewind time and go back to when I first left work in 2012.


Things I’d Change If I Could Do My Retirement Differently

1) Work at least one more year. In 2013, I wrote about the trap of the one more year syndrome where people can’t leave their jobs due to the money and security it provides. It’s always one more year to see if you can get a promotion or one more bonus to feel more secure financially that locks people in.

I left work at 34 years old. Now that I’m almost 42 years old, I look back and think how absurdly young that was to retire. Leaving a good job at that age now seems irresponsible and reckless.

I left because I was sick of office politics, bored with my job, and wanted to do something new. These reasons all sound like I was an entitled, impatient brat. Suck it up already, I may have told my younger self. But in my defense, I had already been with my firm for 11 consecutive years.

Working for one more year would have given me more time to prepare for my post-work future.

I would have lived like a pauper my final year and saved another $100,000+ for retirement. On my firm’s dime, I would have gone on more international business trips, taken out for lunch or drinks all my colleagues, competitors, and clients I had gotten to know over my 13 years in the business, and generally savor my final year at work.

Instead, I now feel like I rushed my departure. I only came up with the concept of negotiating a severance in November 2011, five months before I ultimately did. Therefore, I made some mistakes like taking a week of vacation the year I left. This action ultimately resulted in me receiving a week’s worth of pay less in my severance.

If I had stayed at least one more year, I would have aggressively tried to find a new role within the firm in a different office. It was always a dream of mine to work overseas since I grew up overseas for 13 years.

If I had been able to find a new job within the firm in Hong Kong, Taiwan, Beijing, or London, I think my interest in work would have been rejuvenated and I could have worked for at least another three years.

If you already know a year from now you’re going to negotiate a severance, your work life could become much less stressful and much more interesting. Think back to when you were a senior in high school when you already knew where you were going to college or work. By leaving so quickly, I failed to uncover more opportunities.

Today, I encourage folks to try and gut it out until age 40 or for at least one more year once you’ve decided to engineer your layoff. If you’re burning out, take a sabbatical or an extended vacation more often to recharge. Not only will your finances be stronger, but you’ll also be able to eliminate more completely any potential work regret and maximize your chances of never returning.

2) I would have tried to have children while working. One of my regrets was waiting until 37, or three years after I left work, to try having children. My wife was 34 at the time and had just negotiated her severance.

We waited so long mainly because I was overly focused on my career. I didn’t think I was mentally ready to be a dad without first having an enormous financial buffer. Logically, I felt that having children would delay my permanent escape from work.

Friends kept telling me that once their children were born, they felt they had to work until they graduated college. Working for another 21-23 more years sounded like a prison sentence! Therefore, I decided to avoid prison altogether and selfishly focus on me.

But there’s no escaping biology. The chances of conceiving declines every year one waits. For the average couple, it takes about 7-8 months to get pregnant. Staying pregnant is another challenge. A prayer to all the unborn children who never made it. For us, it took almost three years to have our son.

I would have preferred to be a first-time dad in my early 30s than at 39 years old. Yes, I wouldn’t have been able to spend as much time with him as I do now since I’d be thick into work. But being able to spend a greater percentage of my overall life with him would be priceless.

Having our son while I was still working would have likely made me better appreciate work and all its benefits more. My wife could have taken three months of paid maternity leave. I could have also taken one month of paid paternity leave spread throughout the first three months of our son’s life. When you’re working to take care of the person you love most, you can’t help but cherish your job more.

If your finances are not bulletproof, having a kid when both you and your partner don’t have jobs will likely make you feel extremely stressed. Going from a dual income to single income is also very stressful. I definitely felt more financial pressure after our son was born in 2017, regardless of our retirement income.

Although work is a luxurious safety net for parents, I’m sure I would have eventually started resenting work for keeping me away from our son. Therefore, if I negotiated a severance at least a year after my son was born, I think I would appreciate my early retirement even more.

In retrospect, I would have ideally liked to have my first at age 33, have another little one by age 36, and like my job enough to retire at age 40 after 19 years with my firm. A severance package after 19 years would have been so sweet!

3) I would have worked on my side hustles sooner and more aggressively. The key to maintaining a steady state of happiness is being able to consistently forecast your potential misery and taking steps beforehand to counteract that misery. Ideally, we can all consistently plan 3-5 years ahead. But it’s not a natural act.

I didn’t start seriously forecasting my misery until 2008 after the financial crisis hit. Before then, I was just a super motivated guy who wanted to climb a never-ending corporate ladder for bigger titles and more money. Until then, the correlation between effort and reward had been strong.

After the stock market started melting down, I realized that no matter how well I performed, I was no longer going to get paid and ascend at the rate I was used to. Instead, I would stall out in my career and actually get paid less the more I did because the industry was in a structural decline.

The good times up until 2008 had made me too lazy to start Financial Samurai until 2009. If I had started Financial Samurai in 2006 when I first came up with the idea, perhaps I would have felt much more settled than I did when I left work in 2012.

With more financial certainty, more confidence, and a clearer purpose, I may have had the guts to try having children three years sooner as well. But the desire for money and the necessity to live in an expensive city for this money got me.

Some of you might think I’m being too hard on myself for not foreseeing the recession and starting to work on my side hustle sooner. But ever since I started in the finance industry in 1999, I’ve always felt my years were numbered because of the accompanying long hours and great stress.

Today, Financial Samurai is an established site. But goodness knows how much work and luck it took to get here. Without some lucky breaks, Financial Samurai could have easily died.

Related: 10 Reasons Why You Need To Start An Online Business Today

4) I should have bought more real estate in 2012. Because I was so focused on engineering my layoff in 2012, the last thing on my mind was leveraging up to buy more property. In fact, I tried to sell my primary residence in 2012 but couldn’t because the market was so soft.

If I planned on working until 40 years old, I would have had greater financial confidence to buy at the bottom of the existing cycle. A $900K rental property I would have bought in 2012 would be worth roughly $1.6 million today.

The failure to buy in 2012 was partially offset with a property home purchase in 2014 and continued contributions to my tax-advantageous retirement accounts. But boy could I have supercharged our net worth if I not only bought more investments back then but also worked five more years through a breathtaking bull market!

San Francisco Median Home Price 2019

5) I didn’t fully capitalize on my position as an early retiree. Although I’ve been writing about early retirement since 2009, Financial Samurai is often left out of the mainstream FIRE conversation because I write about so many topics in addition to early retirement.

I’m more focused on wealth maximization through equity investing, entrepreneurship, career strategies, and real estate. Over the past couple of years, I’ve discovered new joy talking about family finances and estate planning.

Once I retired early, I felt like there was no need to talk incessantly about early retirement. Instead, I just got on with my life because my goal of financial independence had been met.

Further, I didn’t want to rub it in people’s faces that I was done with work. Offline, after a year of telling folks who asked what I did that I was retired, I started changing my response to I’m a writer or a tennis coach to feel more comfortable.

But if I had had the foresight and the chutzpah, I would have written more about early retirement life to better brand this site and boost its traffic. I should have been more proactively self-promoting, but I didn’t because it felt unseemly.

I also naively believed more people would give Financial Samurai more credit for being one of the pioneers of the modern-day FIRE movement. But just like at work, those who self-promote the loudest, tend to get the most attention. While those who stay silent and believe their good work will get them recognized usually get left behind.

Despite half the U.S. population living on the coasts, I don’t know many if any early retirement bloggers or people living off investment income in areas like San Francisco, LA, Boston or NYC. As a result, I sometimes feel like I’m on an island. It’s more fun to have a tribe.

As a father now with rising costs to cover and a spouse who is an amazing full-time mom, I need to focus more on monetizing this site going forward. I’ve been way too lackadaisical about generating revenue due to our sufficient retirement income and my desire to only write about things that interest me.

All told, I’m sure I’ve left at least $1 million on the table by being so carefree with this site. It’s time to be more selfish for my family.

Live In The Present, Plan For The Future

Why is it that when we’re younger, we always seem to feel like we’re in a rush to get things done? We’ve got to retire as early as possible, or else! Maybe it’s because we lack patience and feel that we might all die an early death. I certainly felt like retiring early was a hedge against an untimely demise.

As I look forward, one of the main things I can do to mitigate my retirement mistakes is to live as long and as healthy a life as possible. If I can find some way to extend my life by five years, then everything will have worked out. Too bad I’ll never know for sure whether I made a difference in my longevity.

On the positive side, maybe leaving work six years earlier than ideal helped extend my life after all. When I was 33, I started sprouting grey hairs. My hairline was also receding. But by age 36, all my grey hairs went away and my forehead stopped growing bigger probably because my stress level went way down.

The older you get, the more you will feel the race against time. The good thing is that money and status gradually fade away in your personal hierarchy of importance. Desiring to spend more time with family and enjoying more free time is a natural part of life.

If you’re looking to retire early, please ask yourself the following questions:

1) Why am I rushing to retire early? Am I running away from something?

2) What will I do after I retire early? Am I running towards something?

3) How will retiring early change my life for better or worse?

4) Am I sacrificing too much to retire early?

5) Have I gained enough perspective from those who’ve already retired?

When it comes to retiring, there are no perfect answers nor is there perfect timing. You can only do your best with the information you know at the time. It’s only after several years of living an early retirement lifestyle that you will know what you could have done differently to make it an even better one.

Stay optimistic. Live in the present. And consistently spend time planning for the future. Chances are high you’ll live to see another great day.



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