Crash Course in Wisdom: My Own Redesigning Retirement Story

When I think about retirement, my mind goes back to my childhood summers. My grandfather retired first, and my grandmother, after 30 years of service, kept right on working. Retirement, in her mind, meant giving up the lifestyle she’d grown accustomed to and she wasn’t ready to do that. But she always took summers off. She saved up weeks of vacation, and she and my grandfather would spend those long, golden months with us kids.

It took a while, but my grandmother finally retired. What I remember most is how she spent that time traveling with her sisters. When she was home, she always had errands to run and a list of things to accomplish each day. She never really settled down, maybe she slowed down a little, but in my eyes, she seemed to have more freedom to live. That became my first picture of an ideal retirement.

Freedom is my picture of a healthy, wealthy retirement: summers with the grandkids, spoiling them with time, stories, and adventures. To this day, I still dream about being a “rich grandmother” whose greatest joy is pouring into her grandchildren.

I’m still dedicated to it, but it may look different. I’ve got about ten years before I retire and maybe seventeen before I can claim Social Security—if it’s still around. At the beginning of this year, I sat down with my financial adviser and came face-to-face with my retirement plan. I learned, I’m not on track to retire rich. I’m barely on track to retire middle class. That realization forced me to make some tough decisions, and I want to share them with you because maybe you’re facing something similar.

Decision 1: Accept That the Original Number Has to Change

When I first started planning for retirement, I had a magic multimillion dollar number in my head. The amount I thought I’d need to retire rich. But life happens. I went back to school for my master’s degree so I could become a therapist. That $60,000 tuition was an investment in myself, but sometimes I wonder what it would look like if I had put that same amount into my IRA. I might feel closer to my “rich grandmother retirement” than I do now.

I may not reach the original number I dreamed of, and that’s okay. Retirement planning is not about perfection, it’s about adaptation. What we think will happen 30 years from now rarely does, but it can still be beautiful.

Decision 2: Get More Creative With My Retirement Plan

Since I’ve been a business owner most of my life, I don’t have decades of 401k contributions or employer matches to lean on. That means I’ve had to consider alternative tools. Instead of relying solely on my IRA, I’ve increased my contributions to other vehicles like cash value life insurance and even what it would look like to use an annuity to create that pension like income. 

Diversification is the key here. I’m not putting all my eggs in one basket, especially when the market can be unpredictable. I’m also not expecting one vehicle to do all the work. My strategy is to have some investments that are aggressive, some moderate aggressive, and some pretty conservative like a 5% whole life policy that will never match the S&P500. With a little creativity that policy can help fund my lifestyle in retirement, plus give my grandkids the rich life I dream of for them when I’m gone. 

Decision 3: Commit to Funding My Retirement More Consistently

Stopping my retirement contributions while in school was necessary at the time, but now it’s on me to catch up. And I’m not alone. According to the Federal Reserve, only 31% of non-retired adults think their retirement savings are on track. That means nearly 70% of people are either behind or unsure. 

I don’t want to live in that uncertainty anymore. I’ve committed to being more disciplined about funding my retirement every single month. Even if it’s just $100, I have to keep adding so it has the fuel it needs to grow. And because I’m a business owner, I also set up a solo 401k plan. That means I can contribute as both the employee and the employer, which helps me catch up in ways my IRA can’t. So now my strategy is layered: I’ll continue adding to my IRA each month, paying my cash value life insurance premiums, and contributing to my solo 401k—while matching those contributions on the employer side.

Now if you have an employer, whether it’s government or private sector, you might feel you’re safe. However, I just met with a financial therapy client who thought she would be able to retire at the end of the year. She had left her retirement up to the government pension plan. She never checked in on it to make sure she was on track. She and I sat down to design her next chapter and it turns out she’ll need to work 6 more years. If she would have looked at her retirement a few times she could have made the necessary changes needed to retire at her ideal time. 

Decision 4: Be Willing to Work Longer

This was a hard pill to swallow. Like many people, and my client, I thought I’d stop working at a certain age. But the numbers revealed I may need to work a few more years than I originally planned. It’s not great news, but it wasn’t a surprise. I knew I was behind, and I’ve seen what happens when retirement savings get neglected. I don’t love the idea of working longer, but I love what I do, which makes it easier to accept. My client, on the other hand, hates her job and feels like every additional year is torture.

Working longer doesn’t have to be punishment, though it can feel that way if you’re unhappy in your work. That’s where financial therapy comes in. If you discover you’ll need to work beyond your original plan, you may also need stress management tools to help you cope. And on the positive side, continuing to work can also mean staying engaged, relevant, and connected like it did for my grandmother.

Decision 5: Consider Retirement Outside of the U.S.

This is my biggest and boldest decision yet. If I really want to retire rich, or even comfortably, I may need to think beyond America’s borders. Housing costs, healthcare, and day-to-day expenses can be significantly lower in other countries. So I made a list of places I’d be open to living and started exploring.

I’ve already spent time in France, and next month I’ll set out to work remotely for a year in the next country on my list. By the time I’m finished, I’ll have narrowed it down to four strong possibilities.

Of course, this shift isn’t perfect. My grandkids will still live in the U.S., but maybe that just means summers are even more adventurous. Either they’ll come stay with me and get an education that goes far beyond what they could read in a book, or I’ll spend my summers back home with them. Either way, I can carry forward the same tradition my grandparents gave me.

Why I’m Sharing This With You

I’m telling my story because maybe you’re 10 years away from retirement. Maybe you just retired. Maybe you’re already 10 years in. Wherever you are, I want you to know it’s okay to change your mind.

The world has changed. There are more options than ever before, and many of the obstacles we once imagined aren’t as big as they seem. America may not be the dream it used to be, and for some of us, retiring abroad isn’t just about saving thousands of dollars a year, it’s also about choosing a healthier, freer way of living.

Where You Can Start

If you want to begin rethinking your retirement, here are two simple steps you can take right now:

1. Take the Money Mentality Quiz. This will help you understand your strengths and challenges when it comes to money. Then you can address them head on so they don’t negatively affect your retirement.
   
   
2. Complete the Redesign Retirement Questionnaire. There’s no obligation, no pressure, and no judgment. You won’t get bombarded with emails. You’ll simply walk through the questions you need to ask yourself about your retirement plan. You can do it in the comfort of your home and contemplate your next chapter and what decisions you may need to make.
   

And if you want support, there’s a group of us doing this work together. You don’t have to go through it alone, and you certainly don’t have to lose sleep over it. But if you are losing sleep over it, we have a tool for that in our group too. I can share it with you if you complete the Redesign Retirement Questionnaire. It’s free too, so just let me know you’re not sleeping and I’ll get it right over to you.

Final Word of Wisdom

You can’t invest in the past, but you can redesign your future. Retirement isn’t a finish line, it’s a lifestyle. It can look like summers with your grandkids, mornings in a café in France, or a little bit of both. If you complete the questionnaire you’ll get to mentally design a retirement that reflects you, your dreams, and the wisdom you’ve gathered along the way.

Whether you make any changes or not right now, the most important thing is that you’ve decided to face the truth about where you stand. If you do make changes, then it’s important to acknowledge that you took a bold step. You chose to redesign your retirement so you can feel free, not fearful, about the years ahead.