How I Retired Early at 55

I had always planned to retire at 65. In my 30’s I decided I didn’t want to be an “old lady” selling marketing in the latest technology. I started my business at 26 years old and (after awhile) made a decent living from creating websites, as well as branding and marketing small businesses. About 5 years ago, I moved up my retirement age target to 55-57, and successfully retired at 55 last Fall.

Why did I move up my retirement by 10 years?

Well, there’s three reasons.

1. I remarried, and my husband is 12 years older than me. I planned to travel after retiring and it may not be as fun for him when my husband approaches 80 years old.
2. COVID and post-COVID effects on my business were mentally exhausting. I was worried the stress was starting to take a toll on my physical well-being too.
3. My father unexpectedly died at the age of 76. His parents lived into their mid-eighties and nineties. His passing moved up my life clock expectations.

Preparing for retirement

The main thing we were worried about was “could we afford to retire”. My husband was already 65, I had 12 years before I could tap into social security and my retirement accounts. We sat down and drafted a budget, focusing on expenses and income we have that didn’t include our paychecks.

For expenses we wrote down everything we spend money on, including subscriptions, hobbies, eating out, medical insurance, food and gas. We guesstimated some things but we focused on agreeing on a number as realistic as possible.

Next, we wrote down our monthly passive income. This is money we earned but not from our paychecks or businesses. We included interest on our savings accounts, CDs and dividends from investments. It would also include pensions if we had any (but we don’t). We also included my husband’s Social security income, since he was planning on taking it by the time we retired.

Now for the math part… once we paid off our mortgage, our basic expenses didn’t exceed our projected income. However, if we wanted to keep going out to dinner or to travel, we’d need a bit more passive income. So, we moved our money around to get a better return. We also knew we’d need to sell our businesses (instead of closing them) to feel financially confident we could retire.

Transitioning into retirement

Our main focus was to sell our respective businesses. We spent 3 years tightening up processes and financials. We also got assessments and then started looking for the right people to purchase our businesses. And miraculously we both found the right people around the same time.

For mine, after the sale I negotiated a 6-month transition period where I would be reimbursed for a specific fee, in two phases. Because I tend to overwork, I structured the compensation to entice me to let go. (As in, I’m not getting paid to do this.) Even still, it was challenging.

Phase 1: I still want to be needed.
I needed to let go, I wanted to let go, but I also loved the feeling of being needed. I started filling my mornings with workouts, to help me stop thinking of what was going on in the morning meetings.

The afternoons were more challenging, I was usually scheduled for random meetings through the week, and the meetings were never back to back. So I couldn’t unplug mentally during work hours, even if I wasn’t on the clock.

Phase 2: Learning to set boundaries.
After one team member kept setting meetings for Friday afternoon around 3 – 4, and my compensation dropped a bit more, I set the boundary that I wasn’t available on Friday. I scheduled weekend trips and day trips to prevent me from being available.

This was lovely because I experienced two months of 3-day weekends, helping me to prepare for enjoying being work-free.

Phase 3: Filling time.
My transition role was to be available to answer questions and attend meetings. At first, I was like a caged Cheetah pacing around bored in-between the times I was needed. My husband would encourage me to go for a walk but there’s only so many times you can walk the neighborhood without being creepy. I finally started to figure out activities that could fill my in-between time.

• Chores:
  • Food shop
  • Prep for dinner
  • Laundry
• Active:
  • Kayak
  • Short hikes
• Creative:
  • Draw and paint
  • Start a blog
  • Knit and crochet
• Passive:
  • Read
  • Sit outside
  • Meditate
  • Research hobbies
  • Plan weekend and vacations

I kept a rolling list of things I could do in-between meetings. Having this helped me to stop pacing like a Chetah as much.

Phase 4: I’m done and ready to move on.
Even with these strategies I found myself thinking about work, and what was worse there wasn’t really anything for me to do. I didn’t have a fulfilling role, so I made the leap into full retirement instead of negotiating another retainer contract.

Actually retiring

Saying you want to retire, and then actually retiring is a bit scary. I was still struggling to fill time. So I knew I needed a plan for the first three months of retirement.

Month 1: We traveled. We spent 10 days on the road, visiting family and new places. Then we enjoyed the beach and sun at our Florida home. This was great, and I highly recommend doing this to separate yourself from work mentally.

Month 2: I had surgery. There’s nothing like scheduling a surgical procedure to force you to “stop”. This wasn’t so great, but necessary. After I was feeling a bit better, I still needed to keep busy, so I knitted most of the shawl below. (I’m adding crochet stitches to the top part, to finish it off.)

Month 3: I found new challenges. I joined our HOA Board and also leaned into creating my blog and socials. This gives me a purpose as well as something to do.

Three months in, am I happy I retired at 55?

For the most part yes. I don’t miss the work headaches for sure, but I do miss the people interactions. I definitely believe there’s no right age to retire. Some people live to work, others work to live, and the rest are somewhere in between.

For me, I am more of a live to work person, so I enjoy having challenges and a routine of things to do. The key it seems is to “have a purpose” and find something fun that you enjoy doing. But then again, I’m only three months in. Stay tuned for updates. 🙂