Gift of a Leap Day Letter

Have you ever written a letter to your future self? Trust me when I tell you it can be fun, and February 29th is the perfect day to pull out paper and pen. Write it today and open it on 2/29/28. Because even though we often forget, every single one of us is solely responsible for writing the next chapters of our own lives. Sure, life will throw us curve balls, but how we respond and where we place our daily focus will ultimately shape our journey.
 
Why do I think writing a letter to your future self can be both fun and helpful? Because I’ve tried it.
 
On the front end, as you decide what to write, you get to dust off your dreams. To really think about what you’d love your life to look like over the next four years. Then you can seal up the envelope, stick it on a shelf, and go about your day. When Leap Day rolls around next time, pulling out those handwritten sheets will feel like an intimate visit from your younger self.
 
An eight year old letter is even more fun to read through.
 
On the morning of February 29, 2016, I sat at a crowded conference table in the basement of a high-rise office building in downtown Denver, Colorado. I was working with yet another new team and it was my first time meeting most of them. With twenty-five years of experience in corporate America, I could play the part, but I didn’t want to be there. I braced myself for a long day of dry discussions.
 
But the executive running the show that day kicked us off with a surprising exercise. He gave each of us three sheets of paper and an envelope, along with a challenge to write our future selves a letter. After the allotted time, he’d collect our sealed envelopes, hold on to them for four years, then return them to each of us on February 29, 2020.
 
What a refreshing way to kick things off! At least I thought so, but I heard a few groans, too.
 
I took the assignment seriously, banging out three full pages of handwritten notes to myself. The only rule I broke was around turning in the letter. I’d been around tables like this for long enough to suspect our “world” would probably look very different after another four years, and the likelihood of that envelope finding its way back to me was slim. Instead, I slipped it in my briefcase and brought it home.
 
It’s always best to control our own destiny!
 
A Leap Day Letter is for your eyes only. But today I’m going to take a leap of faith (sorry, I couldn’t resist) and share with you the nine items I wrote on that long ago day, and how things are turning out, eight years later. Remember, I had to write these out quickly, without time to prepare, but I suspect most are quite relatable.

• 2/29/16: “Control my time.” I longed for time freedom. At 49 years old, I was sick to of others controlling my schedule. I wanted to work with a more flexible schedule set by ME.
  • 2/29/20: Still stuck in the 8 to 5, but I had a written escape plan and I was getting things lined up to make the leap.
  • 2/29/24: It’s 9:16 a.m. and I’m working on my laptop in my living room, in my bathrobe, with our sweet little Yorkie close by.

 

• 2/29/16: “Proud to be a published author.” But all I had at the time was a very rough manuscript in my desk drawer at home and no clue how to take it from a Word document to an actual novel.
  • 2/29/20: Four novels published with a fifth written and in the editing phase.
  • 2/29/24: Writing full time and ten novels published with the eleventh releasing soon.

• 2/29/16: “Do work that adds significant value to other people’s lives.” I was burned out in my job. It was hard work, but the output never felt meaningful. It wore me down.
  • 2/29/20: Countless role changes occurred over the four years since I’d sat around that table in 2016, and they were all at the whim of others. I knew I needed to make a change, but I was terrified to walk away from my salary and benefits.
  • 2/29/24: I’m a full-time author. When I turned 55 in the 2021, I turned my back on what I knew was a false sense of security. I’d always regret it if I didn’t take the chance.

• 2/29/16: “Healthy lifestyle.” Eating better and getting regular exercise was always a struggle for me. Twenty-five years in a desk job and my fiftieth birthday was looming. Again, I knew I needed to make changes.
  • 2/29/20: I kicked off 2020 with a new Fitbit and the goal to walk a minimum of 10,000 steps a day. Two months in, and I hadn’t missed a day. The new habit would be a blessing in the coming months, when so much of the world shut down. By the end of 2020, I’d walked over 2,000 miles.
  • 2/29/24: Too much of a good thing is sometimes not sustainable. My rigid stance on long daily walks contributed to issues with my feet and legs. I fell out of my walking habit, and I still have room for improvement in my eating habits. But a new walking pad under my writing desk is helping!

 

• 2/29/16: “Solid relationships with Rick (my hubby), our kids, my parents, extended family, closest friends.” Family has always been my #1 priority. We’d likely be empty nesters soon, with all three kids off living their own lives. How could we all stay close?
  • 2/29/20: In 2016, I knew that my dear mom was facing a potentially life-ending illness. She was my rock, and when we lost her in 2017, I had to learn how to do life without her. By February 2020, our youngest was away for her freshman year of college. Within weeks she’d be forced to move home again, so the nest didn’t stay empty for long!
  • 2/29/24: I’ve adjusted to life without Mom, but she’s always close in my heart. We’ve suffered other losses, too, but we learn to adjust. This summer, we’ll celebrate our 35th wedding anniversary, and I even have an exciting new title: Nana!

 

• 2/29/16: “Travel without strict time limitations.” I dreamed of the day when I didn’t have to abide by a PTO schedule.
  • 2/29/20: I squeezed in a bit of travel, but it was still impossible to get away for long.
  • 2/29/24: I’m free! Well, sort of. For example, in the fall of 2023, I visited Sedona for a women’s retreat, Florida for a writing conference, and the Biltmore House just because. Here’s to more travel in the future!

 

• 2/29/16: “Help other working mothers find a different way to support their families without the 8 to 5 grind.” I didn’t know how, but this vision was on my heart. In 2016, I still had kids at home. Throughout my corporate career, I’d find myself encouraging work friends to keep their families first, even when work commitments made it tough.
  • 2/29/20: The theme of midlife reinvention started appearing in my novels.
  • 2/29/24: I still want to encourage women to chase their dreams, no matter their age. I try to write fiction that offers inspiring entertainment and to live my life as an example of the reward in taking chances. How I continue to do this will evolve.

 

• 2/29/16: “Build multiple streams of income vs. relying on a J.O.B., find ways to save money so it can be redirected for more enjoyment, help others, and to take care of myself for as long as I live.” Yes, I am a numbers girl at heart!
  • 2/29/20: Again, I hadn’t summoned the nerve to leave my J.O.B yet, but I was quietly executing my escape plan by doing things like setting money aside from my paycheck every month to use for future insurance premiums when I’d eventually take the leap.
  • 2/29/24: I’m actively building multiple streams of income with every new book I write, each new online vendor I load my books onto, etc. In the future, I’ll continue to implement a wider variety of income streams. It’s dangerous to rely on one income source. Life teaches us all this.

 

• 2/29/16: “Set an example for my kids around building a lifestyle you love vs. spending so much of your precious time working for others on things that aren’t important to you.”
  • 2/29/20: By 2020, I knew my three kids didn’t really believe that I’d ever make the career change I so desperately wanted. I’d talked about it for too long without taking action. That couldn’t continue.
  • 2/29/24: I’m striving to keep my writing career as a viable option, proving to them it’s possible to find work you love. We all need some level of monetary reward to pay the bills, but I want to show them that work can be so much more than just tolerating unrewarding work in exchange for a paycheck. In some ways, my new gig is much harder than my old one, but the rewards are so much greater.

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Today, my life bears little resemblance to the one I was living as I sat around that conference table in 2016. I’m now 57 instead of 49. Time has a funny way of slipping away. My work is so much more creative now than it was back then. My days are my own. Some old problems have fallen away, while new ones have cropped up. That is what it means to be alive. Overall, I’m happy with the progress I’ve made over the past eight years.
 
Did that letter I dashed off to myself on 2/29/16 make any difference? I like to think so. There is always a benefit to pausing and thinking about what you want next in your life.

Did I write a letter to myself on 2/29/20? I thought so, but I can’t find it. Maybe I wrote it while at my desk in my old office building. Things were getting a little scary right then, and within a couple of weeks, we were all sent home to work. Perhaps the letter got lost in the shuffle. I never went back to that desk. I worked from home until I quit in October 2021.

Maybe I’ll find the letter from 2020 someday, tucked away in a drawer. It doesn’t matter. What matters most is that today I’ll pull out three fresh pieces of paper and write myself a new letter to open on 2/29/28. I have so many more dreams to pursue and I never want to stop growing or learning.
 
I encourage you to find ten minutes today to do the same. Your future self will thank you!
 
Always cheering you on,  Kim