Self-made millionaire who retired at 40: The 5 biggest surprises—'I've let go of the idea of a perfect retirement plan'

Last year, I retired early at 40. It was the most recent in a long line of financial milestones: I paid off $300,000 in debt, became a millionaire, and left my corporate job behind. 

This looks like a success story on paper, but the last year hasn't exactly gone to plan. There have been days that have been wonderful and days when I've melted down. 

A year in, I've let go of the idea of a perfect retirement plan. There have been plenty of surprises, and they've taught me a lot about what is actually important to me.

In the first quarter of this year, I lost about $60,000. I've taught investing classes for years. Despite knowing that stock market dips happen, I was still surprised at how anxious I felt when it happened.

I've learned that it's not as easy to just "set it and forget it" when you are relying on that money for current income, rather than investing for a distant future. 

Many financial advisors recommend keeping three to six months worth of cash savings on hand. We have more than a year's worth saved. That cushion is giving me the space to not panic or make reactive decisions. 

I plan to keep drawing from cash while giving my investments time to recover. It helps me stay committed to the long-term strategy, even when it feels uncomfortable in the short term.

I've gotten a lot better at managing my discomfort by maintaining a consistent monthly budget and only looking at my investments when I make a big purchase.

I have a chronic condition. When I was thinking about retirement, one of my biggest worries was making sure I wouldn't have any gaps in my care. In the absence of employer insurance, we had to get a little creative. The solution was more patchwork than I anticipated.

First, we spent four months researching and comparing private insurance plans. Then, last year, we visited Malaysia. One of the main reasons for the trip was to get a comprehensive medical screening to get a clearer sense of what conditions we might be susceptible to in the future. It cost $769 for both of us, cheaper than it would be back home.

Then we were able to provide the screening results to our new physician, who is based in Las Vegas, where we are moving later this spring.

We decided to try a concierge primary care doctor. It's a monthly subscription, and an additional cost that we didn't have before we retired. But having someone I can talk to anytime has brought me peace of mind. 

Having a schedule that isn't tied to a paycheck is wonderful. But for the first few months, I found myself struggling to organize my days in ways that felt meaningful to me. I wanted to have a clearer sense of direction.

It took some trial and error, but I landed on a strategy works for me. Each quarter, I choose three categories to structure my schedule around: my health, my hobbies and my passion projects.

Last quarter, I focused on yoga, improv and planning a big event for the personal finance and entrepreneur community I have built through my platform CRUSH Your Money Goals. 

Even though I don't need to work anymore, I decided to continue my coaching and events businesses. The biggest reason is that I wish I had something like this when I was in the corporate world. I also get a lot of joy out of mentoring. I do it because I love it, rather than for profit.

Early on, I felt some pressure to show everyone how awesome retirement was, to prove that we had made a good decision.

I realized how much I was relying on external validation from others to make me feel I had made the right choice. This is something that I'm still working through. Journaling and therapy have helped a lot. So has redefining what I want my community to look like now. 

I don't have co-workers anymore. Most of our peers are not in the same stage of life that we are. That's okay, but it can be isolating. So I've really focused on meeting people and cultivating friendships through my hobbies and interests like comedy, yoga, sports and music. 

I did wonder if retirement might be boring. It turns out I have the opposite problem. There are too many things I want to do. I want to sing again, I want to play pickleball and volleyball and I want to travel. I'm also a huge K-pop fan.

This is not ideal for my wallet, but I made a decision I didn't expect. Instead of being scared to spend on things that bring me joy, I'm leaning into it. I'll see BTS when they go on tour and go to a few other concerts, too.

I'm going to say yes to experiences that fill my cup. It's okay if I have to adjust my budget a little next year. I've decided to let myself enjoy the time I worked so hard to create. Because for the first time in 20 years, since I started working, I actually can.

Bernadette Joy is the author of "CRUSH Your Money Goals″ and a personal finance expert and investor dedicated to helping you beat burnout and reach financial independence. You can find her on Instagram, YouTube and LinkedIn.

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