Shawn Jenkins Blog

Shawn Jenkins Retirement

My First 18 Months of Early Retirement

It doesn’t seem that long ago that I was reading a blog post by Brandon, the Mad Fientist, describing his first year of retiring early. At the time I was working hard to build the company I had co-founded. 

It seemed foreign to me to even consider shifting gears from high growth and fast paced to slow travel and relaxed living. However, the thought of transitioning to a slower pace, being able to take my kids to school each day, having long periods of unscheduled time—these daydreams began to seep into my soul. 

The appeal of the simple lifestyle was an enormous draw. I had learned to live with pressure and complexity. Now I wanted to learn to live with quiet and calm. 

So a little over 18 months ago, I took the leap and retired early. With work almost 550 days behind me, I thought it was a good time to summarize what that experience has been like, how I handled the transition, and some of the surprises along the way. 

At some point, I think the community will invent a better term than “retirement” to describe what people are doing when they intentionally step away from their careers while still in their prime working age. When I retired, I hardly stopped doing things. In many ways, I do more things and have a much wider variety of experience than I have ever had before. Until that new term comes along, I will happily use “early retirement” to describe my experience.

People and Places

The biggest concern I had about making the transition to early retirement was missing my friends at work. I absolutely loved the people I worked with—and still do! I never even considered life without them until I began to contemplate early retirement. For me, our company was part of my family. As a co-founder, I always felt that the business was like one of my kids. I still feel that way.

It may have been the symbolic timing of the business approaching its 18th “birthday” (we started the company in 2000) that awakened me to the fact that it was time to let it go, let it learn to be independent. In many ways my story of finding my independence is that of a father allowing their child to become independent. The biggest hurdle was the responsibility I felt to our associates. And yet I knew that to truly see how well we had built our company, I had to see it perform from a seat in the stands.

This awareness was made more pronounced by the fact that I felt it important to allow the leadership team to take the business in directions they felt best. I had seen entrepreneurs hire people to run their businesses but then smother them and second-guess them to the point of frustration to all. I was determined to take the harder road and remove myself from the day to day and even long-term strategic decision making. 

As I made my transition, so came the most difficult part of the entire process: not being with my friends at work. This was, and still is, the hardest part of the experience. 

This part of the subject, especially for founders of companies, warrants a deeper treatment of the decision process, the strategy, and the emotions than it can receive here. I plan to write more on it in future posts, but for the sake of sharing the punchline, here’s my quick insight: a) you cannot half do this—you have to rip the band-aid off all at once; and b) it’s harder than you think when it comes to the relationship loss but easier than you think as far as shifting to less busy activity. Said another way, I didn’t miss the work all that much but I did miss the people a ton. And miss may not be the perfect word here either. It was more of an awkwardness, like learning a new language or learning to breathe underwater with a scuba tank for the first time. 

My life was completely wound up in the complex set of relationships of long-time associates, customers, partners, investors, and the way I related to the community from my role. As I clipped that cord, there was no guidebook as to how to reset my mind and my soul. I had trained myself to operate almost exclusively from that vantage point for close to 20 years. And then all of a sudden, nothing. 

At first, I struggled when asked the question, “What do you do?” I didn’t want to keep introducing myself as a “former” anything. I was initially hesitant to use the word “retired” but eventually just got over it, and now I smile and say, “I do nothing!” (This always begins a great new conversation.)

I had the intention not to become isolated by the vacuum created in my schedule, but I didn’t want to replace it with another company or activity that was similar to what I had become accustomed to. Therefore, I pushed myself to connect with a new community of people, namely the FIRE (Financial Independence / Retire Early) community.

It so happened that a few months into my decompression phase I heard Jonathan and Brad at the ChooseFI podcast announcing the dates and location of JL Collins’ Chautauqua event in Greece. My wife and I signed up the same day, and before we knew it, we were standing at the foot of Mount Olympus meeting a host of new friends on their own personal FI journeys. 

This has led to some fantastic new friendships and life experiences that continue to open new doors.

Now, 18 months in, I have begun to reconnect with some of my old coworkers, and so my life is what I consider a healthy mix of lifelong friends and associates along with a growing group of new friends and collaborators on new projects.

In a very unexpected twist, I also recently ran into a high school friend whom I hadn’t seen since graduating. As sad as it sounds, I hadn’t kept up with anyone from either high school or college. My life was always out in front of me, and I just never stopped to enjoy the texture of my old friends. 

My buddy from school and I got together over a beer and fish sandwich in Daytona Beach, FL, where we grew up, and now we see each other often when I visit. I also received a note from a college friend who found my blog, and he and I have begun to catch up.

I think I was moving too fast, and more practically, I was just living too far in the future to stop and enjoy these conversations. I’m not much for Facebook, but I’m just now learning the slow joy of sharing stories with friends from my formative years.


One of the main ingredients in my motivation to retire early was a desire to create a healthier lifestyle. I had periods of focused health improvement over the years. These usually came in the wake of poor health due in part to stress and demanding schedules. I tended to put the responsibilities of my work over those of my personal health.

In transitioning out of my job, I wanted to get at the root of the stress and eliminate it. I would often feel a physical jolt of cortisol entering my bloodstream on very stressful days. This led to lack of sleep, weight gain, and a host of related nuisance ailments such as an ongoing peripheral neuropathy. All jobs have stress, so I don’t think my situation was all that unique. Even though I loved my job and company, the ever-present alertness on things like data security, complex projects with compressed deadlines, and ensuring everyone was healthy and happy had a way of wearing on me.

My thesis was that if I eliminated the source of the stress then I would take the excess cortisol out of my body and be in a better position to create a new, sustainable, healthy lifestyle.

The results on this front came faster and easier than I predicted. I had set in my mind this concept of a two-year “deep rest” period. I didn’t want to rush into some difficult and unenjoyable diet and routine that I couldn’t sustain. I simply wanted to eliminate the stress and see how my body reacted. Similar to a scientist isolating a single variable in a lab experiment.

In the first six months, I experienced what I now call a 10-10-10 improvement. With little effort I lost ten pounds, my blood pressure came down ten points, and my resting heart rate lowered by ten beats per minute. 

In the next 12 months, I put together a more purposeful eating and exercise plan and lost another 12 pounds, improved my blood pressure further, and continued to lower my resting heart rate. 

I started by seeing a personal trainer three times a week. I’d ride my bike the two miles from my house to the gym, and that combination of being outside on my bike back and forth to the gym along with the one-on-one training really built an excellent set of habits rather quickly. It was also very nice to have an open schedule and choose times outside of the busiest early morning on-the-way-to-work schedules.

I tackled diet second and began with a lot of fruits and veggies, mostly in fresh homemade juices. I had watched Forks Over Knives and Joe the Juicer from Fat, Sick, and Nearly Dead a few years earlier, so I simply picked that routine back up a few months in to early retirement. My wife and I began shopping together, and I learned to love seeing the rich colors of the produce.

After my six months of de-stressing, I got even more aggressive with my diet by doing a series of juice fasts from three days up to ten-plus days. I also added in the premade five-day Fasting Mimicking Diet from ProLon

Each time I did more experimentation with diet and forms of exercise, I learned so much about myself and my body. It was helpful to have the time to try different things out and not have to jam the new techniques in between busy work periods. What’s even better, I haven’t had to fight to maintain the results. 

I know a lot of people are looking for that one perfect adjustment to make or that one perfect program to follow. For me, it’s more about the experimentation and lifestyle of improvement.

Freedom from Email and Scheduled Events

The most practical thing I wanted to accomplish by retiring early was that I wanted to no longer experience the constant presence of work email and corporate calendared events. If I could wave the proverbial magic wand, I just wanted to drop Microsoft Outlook email and calendar.

If you’ve ever had the fantasy of deleting Microsoft Outlook from your computer and phone, I can affirm here and now that it is indeed as amazing as you imagine it would be. I haven’t used Word, Excel, or Outlook for over 18 months, and it is the gift to your soul that keeps on giving.

My first day of early retirement was January 1, 2018. So for Christmas 2017 I went to the Apple store and bought a new personal iPhone. I had carried a “work phone” for 18 years, and now it was time to set up my post-work routine. 

I gift wrapped the iPhone to myself, and on Christmas day I so enjoyed setting it up without any corporate email or calendar. I created new Google accounts, and on Dec. 31, I switched my life over.

Because January 1st is a holiday and businesses and markets are closed, it didn’t feel all that unique; however, when I woke up on January 2nd and held that phone, I felt the relief. I still had the ingrained mental patterns of worrying about the many details of our business and people, but it was pretty wonderful to not have any email, scheduled meetings, calls, or text messages. 

Now, over 18 months later, this is still the most noticeable practical benefit of retiring early.


My motivation for early retirement was not so much about traveling the world. My job had a lot of travel to it, and by nature I prefer to be home. I always made time for some great family trips, so I didn’t feel deficient in this area.

That said, you don’t have to read many FIRE blogs to know that travel is a part of the lifestyle. Honestly, I felt like I could’ve actually just sat at home if we didn’t purposefully plan some travel, so we did. And here are some of our experiences so far:

Colorado Mountain Ranch  

We packed up the family for an adventure at the Smith Fork Ranch. At 7,000 feet above sea level, the views were spectacular. We rode horses into the nearby national forest’s peaks of nearly 9,000 feet. I highly recommended this experience! 🙂

Thessaloniki and Mount Olympus, Greece 

This was our intro to the FI Community at Chautauqua. Read all about it here.

Maui, Hawaii 

This trip was to celebrate my oldest daughter graduating nursing school. Such wonderful people on the island and some of the best hospitality we’ve ever experienced. Two highlights were diving a volcanic plume and an aerial tour of the island. Mama’s Fish House racks up a month-long wait for dinner reservations, but we found lunch to be just as amazing. 


Just being on the water in early March when I typically would have been preparing for an annual user conference was a big milestone. While we saw a few cars during our visit, I would say the island is 90% bikes and well-worn golf carts. The people are so wonderful on the island of Eleuthera. They seem to smile with their eyes in a way I haven’t seen before. 

Daytona Beach 

We did a three-month slow travel at the beach this summer. I grew up here and my mom and sisters are nearby. Mornings over coffee, lunch on the beach, afternoons at the pool, and random dinners for weeks on end. Even better than I imagined. Although my family has always been very close and have always spent just about all of our free time together, there was something about this summer that drew us even closer in a pretty powerful way. I feel like I got to know my family, and they me, in a new and deeper way. I would take it further and recommend to anyone who is considering some sort of sabbatical or mini-retirement to certainly do it. The calm enjoyment of three months with nothing to do but be with your family and friends is an experience like I have never known.

Enjoying a slow day at Biltmore

Biltmore Estate

The Biltmore Estate is a favorite escape for my wife and me. We got away by ourselves and also did a visit with the kids. We continue to pile up memories and photos year after year. 

It’s hard to overstate the difference between traveling with the knowledge work is waiting for you back home and traveling completely untethered. It unlocks a new set of rooms in your mind that allow you to get to know yourself and your loved ones in completely new ways. 

For example, I learned the subtle, unique swimming habits of each of my kids. Because my mind had no other demands, I was able to notice that one of my daughters loves to jump up and down in the shallow end of the pool for close to 30 times in a row while saying a silly phrase. I used to do the same thing. While my youngest son loves to continuously swim under my legs and can hold his breath for what seems like a dangerous amount of time.

That mind space, free from work, allows me to focus my complete attention on the now, and has helped me notice, experience, and grow my appreciation for my family in entirely new ways. And they me. 

Next year we’re considering taking a year to travel the country in an RV and homeschool—or “world school”—our kids. 


(I am not a financial advisor, so this is not advice. Please do your research and design your plan to fit your style and circumstances.)

Time and money are connected. We trade our time to earn money. We then spend our money to buy things that took someone else time to produce. 

I have been surprised how the strategy of investing in this phase of life keeps pulling back to an internal discussion of how I want to (or don’t want to) spend my time.

For example, if I invest in an index fund, it requires zero amount of my time to maintain. But if I invest in a startup company and join their board, I have to attend meetings, review reports, and think about liability. While I am done having a job, I am just beginning to learn how to be a full-time investor (my new definition of FI by the way).

Because my career took me into the world of employee benefits, I’ve spent a lot of time learning about retirement plans, both from a tax standpoint and also the underlying investments. I have also seen the data on how millions of employees elect their retirement savings amounts and investments. 

Also, having taken a company through an IPO, I was able to learn a good deal about how Wall Street operates, how fund managers select companies to invest in, and how their performance works over time. 

My basic conclusion is that owning a wide array of U.S. public companies over a long period of time is a good plan. I have found the best way to do this is through ultra-low-cost index funds from firms such as Vanguard and Fidelity. I have invested a large portion of my personal 401(k) plan in the Vanguard Index 500 fund for years.

In this new phase of my life, I have created a framework of three investment buckets: 1) publicly traded stocks, 2) commercial real estate, and 3) private investments in technology startups. 

For the public company investments, my allocation is simple: I remain 100% in stocks. I’m still young and I’ve grown accustomed to the swings of the market, so it doesn’t bother me when things go up and down. I do this in simple low-cost index funds from Vanguard and Fidelity. 

The second bucket, commercial real estate, is something I already had as part of my portfolio, so the biggest question was whether or not to increase it. Adding more commercial real estate would mean doing some work. Looking for properties, buying existing buildings or developing new buildings would take time. I’ve spent more than a year asking myself if this is something I want to do, especially since I’m “retired” after all. I’ve learned that I really enjoy this area, so I’m beginning one new project. Based on how that goes and how much or how little I enjoy it, I can decide in the future to hold there or do more.

And the third bucket, investing in privately held young technology companies, has been another ongoing internal conversation. On one hand, it makes sense that I should do at least some of this type investing. I understand the industry, I know a lot of people, especially in the HR software space, and I’ve seen the power of this asset class up close and personal. However, this too requires “work” and time. 

For now, I’m passing on startup investing opportunities, but I’ll remain open in the future should I find a way to have fun with it while not getting myself back into an operating role.

Community Service

As my schedule opened up over these last 18 months, I knew I wanted to spend a good bit of time helping folks in our community.

The first and most obvious place to start was with our state’s children’s hospital. My oldest daughter had gotten help from our children’s hospital, both as an infant and also as a teenager, so we’ve always had a heart to give back to those wonderful people. 

In 2015, the board of the Medical University of South Carolina asked if our family would consider making a leadership donation to help build a new children’s hospital here in Charleston. We gladly agreed, and recently we joined the community for a dedication celebration for the new MUSC Shawn Jenkins Children’s Hospital. 

Helping raise money for the Children’s Hospital with my kids on the Y102.5 Radiothon

This community project has been the joy of a lifetime and has given me new meaning about the true value of my work career. Naturally, I’ve been spending a good bit of time on the construction job site, attending events to help raise funds for the hospital, and a host of other activities. I feel tremendously grateful for the opportunity to participate in such a large and impactful project. This has enriched my life a hundredfold.

Another fun project that popped up since I’ve been job free is helping my mom assist some of the teachers and kids at my old elementary school, Port Orange Elementary in Port Orange, FL. My mom has always been very generous with her time in her community, and she’s worked with several organizations supporting kids through her church and the local police department. She now helps my old elementary school by picking up snacks for kids to take home after school and extra food for the weekends. 

The seed for another service opportunity came during our trip to Greece when we met Jonathan and Brad, the hosts of the ChooseFI Podcast. It was a real honor when they asked if I would serve on the board of their new ChooseFI International Foundation. The foundation’s mission is to develop and provide personal finance and financial independence curriculum for kids in K-12 as well as military personnel. I cannot wait to see how this material develops and spreads in the coming years and how many lives are improved through the application of the basic principles of financial independence.

Having the ability to spend more time with these and other organizations adds such texture to life. I’m thankful every day that my business was successful and now I’m able to donate not just money but time to help these platforms for good.


In the book Blue Zones, researchers uncover a set of shared characteristics of people in specific locales who live past 100. One of those characteristics is the concept of “life purpose” or “community role.” 

With that in mind, I want to ensure I continue to keep my mind active and contribute to the multiple communities I’m a part of. It has been somewhat tricky to decide which projects to undertake. At times, I feel like the six-year-old Shawn standing in front of a wall of cereal boxes at the grocery store, painfully trying to choose just one!

Seth Godin has a helpful framework on his blog where he explains his career as a series of “projects.” His books, presentations, online businesses, and courses have been developed over 30 years. His career seems more like that of an actor doing different movies than a professional working for companies. I’m recasting my next phase of life to be a series of projects. Here are a couple I’ve begun so far:


We purchased 275 acres of land near Charleston, and with some friends are creating a regenerative, carbon neutral farm. Read all about it here.

Demo Day at my new gig working for my son!

House Flipping with My Son

My oldest son recently started his own business flipping houses. It has been a lot of fun helping him do the renovations. One hilarious story is when he sold the old stove from one of the houses on Facebook marketplace. He and I delivered the stove in his pickup truck to an elderly gentleman. When we offloaded it for him, he politely thanked us and handed us each a $5 tip! We got in his truck and laughed and felt fantastic for putting in a hard day’s work. Two weeks prior I was in a sophisticated career and now I was the second hand on a used appliance delivery truck and could not have been happier!

Chillin’ in Greece and starting a new project with Alan Donegan

Pop Up Business School 

We met Alan and Katie Donegan on our Greece trip and are now working to bring their two-week Pop Up Business School to Charleston in early 2020. I wrote about my experience attending their school in Houston. Check it out here.


When I was working, I enjoyed blogging and hosting small group meetings on the topics of career growth, personal development, and building a platform for good, so I decided to create a personal blog along the same lines. It’s fun working on my blog and watching it find its way in the sea of online content. The biggest benefit to me so far has been the rekindling of connections to people I haven’t seen in a while. Also, I find that exploring new topics, as well as reinvigorating old ones, helps keep my mind sharp.  

Final Thoughts

At the deepest level, this transition has allowed me to slow down and listen to myself in new ways. When I read books now, I see things from a different perspective; I’m making new friends and reconnecting with old friends. I still have the same inner voice, the same concerns, irrational fears, and anxieties that I think everyone deals with. But now I have the time to sit with those emotions and listen to what they’re trying to teach me. 

I can experiment with foods and routines and exercises and meditation. And when something doesn’t work, I can more quickly move forward and try something else. I feel like an independent scientist in a small lab where the research is solely from natural curiosity.

I think someday we will find a better word than “retirement” to more aptly describe what it means to intentionally step away from the traditional work lifestyle. My days are filled with activities and experiences that are productive and many ways contributory. It’s a form of relaxed leaning forward and advancement. The purest emotion of this experience is gratefulness.

Scroll to Top