Early Retirement Hindsight: What I Would’ve Done Differently

PUBLISHED Dec 21, 2022, 6:22:44 AM        SHARE

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I feel truly blessed to have been able to pull off an early retirement. I take great pride in being able to take the leap at the age of 51. It came after a long career with a less than a 6 figure salary. Still, after experiencing early retirement for many years and knowing what I know now, I often think about what I would have done differently. Allow me to share my early retirement hindsight.

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My Early Retirement Hindsight – The Things I Would’ve Done Differently

I Would Have Set Aside More Cash

It took time to get my retirement footing even with all the research and planning I had done. I retired with just a bit over $20,000 in non-retirement account cash available to me. It was my emergency fund, there in case I had lost my job. That certainly wasn’t an issue anymore with retirement. Looking back at my financial journey, my desire for investment growth had me underestimated how much having sufficient cash reserves can calm one’s retirement transition. Believe it or not, retirement can mess with your mind after spending decades in the rat race trenches.

Everything worked out but in early retirement hindsight I would’ve had $40,000 in cash to get through my retirement transition. It isn’t even about spending it. Instead it’s about knowing it was easily available if I needed it or wanted to spend it without having to liquidate investments.

I Would’ve Prioritized Mortgage Payoff

I never gave early mortgage payoff a thought before retiring. It did get paid down over the years and I refinanced it for the lowest payments possible. I simply figured it best to direct any extra money toward retirement savings and planned for a retirement that included a manageable mortgage payment. We rationalize that we will get better returns than the mortgage interest we save with payoff. That is until we don’t and invested money goes negative as it did when I retired in 2009.

I did prioritize mortgage payoff a few years after my first early retirement by directing the salary of my encore career to it. Years have passed since that payoff date and it still makes me smile. I underestimated the benefits. Yes, we can expect over time, investment returns to exceed mortgage interest. For some people the tax deduction also comes into play, or it used to. But in the end, without a mortgage payment you not only save that interest but you need less in your retirement budget. That means less taxes paid year after year. So much of our having a great retirement is mental. Being mortgage free certainly adds another level of mental freedom.

I Would Forget Any Notions About Loyalty & Leaving A Career Legacy

In early retirement hindsight I really messed up here. I stayed dedicated to the company and job to the bitter end. Even at the detriment of my personal life in the last years. I had built a legacy of good work and accomplishments and didn’t want to slow down and possibly tarnish it. Simply put, as far as the corporate world goes I was a dumb-ass. Nobody really cares and the memory of our efforts quickly evaporate once we are out of sight. We falsely build up in our minds the importance of leaving a workplace legacy because we are in a relationship with the company and our team of coworkers. But the reality is the relationship is just business and survival.

During a time of constant layoffs that were supposedly performance and economic based, I should have said screw the legacy and proactively made myself an attractive candidate for a severance package. All it would have taken was dragging my feet a bit and using the word “NO” when approached with asinine demands a few times. There were certainly numerous opportunities for doing that. In hindsight, had I done that I would have built up my earlier mentioned cash reserve deficiency and put an even bigger skip in my early retirement rat race escape.

I Would Have Gained Pre-Retirement Side Gig Experience

I have had a couple of really enjoyable retirement gigs. But there is one that got away and I wonder, what if? I certainly had a passion to do it and was qualified as it wasn’t anything super technical that required advance skills or education. I was dismissed as a candidate because I was overqualified based on my career and I had no real experience doing it. In early retirement hindsight I wish I had slowly scaled back my career effort and responsibility to make time to do part-time work in this different field before I pulled the retirement plug. It’s probably easier to get a foot in the door part-time while still working. I should have been more selfish with my time and personal desires. I regret not having been able to pursue this target of interest and passion even if in the end it didn’t work out or lasted long.

Looking Back At What I Think Went Better Than I Thought It Would

Embracing Frugal Living – This not only got me to early retirement but has proved a blessing for a great early retirement lifestyle.

Retirement Gigs – When you spend decades in the rat race it is all you really know. I can’t explain how different, rewarding, and enjoyable it is to work doing something you really want to do for only as long as you want to do it.

Social Expansion – Putting in the effort to increase my social circle beyond work is one of the most fulfilling parts of my retirement. Connecting to my community has been an important key to retirement happiness.

My 72t Strategy – I funded my early retirement with an IRA using 72t for penalty free monthly distributions. It is seldom talked about and when it is there’s many cautions. I couldn’t have done what I have done without using this backdoor retirement funding approach.

I am sure there are a few more things in hindsight that I could come up with that I would’ve done differently in this early retirement adventure. There are always ways to have done something better. I can say that I have absolutely no regrets about retiring early or what it takes to do it. When breaking the work-to-old-age norms there is always risk. But done right or as close to it as possible, it is 100% worth taking the risk.

Originally Posted in Leisure Freak


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