5 Tips for Creating a Legacy You’ll Be Proud Of

I’m going to ask you a question that I have personally pondered quite a bit over the past couple of years.

Think about this for a moment: When you die, how do you want to be remembered?

It may sound morbid at first, but I assure you that is not my intent. Rather, I want to give you the opportunity to stop and think about the legacy you’re creating and where you may need to course-correct to live your best life.

Years ago, when I worked a corporate job, I’d spend 10 to 12 hours a day in front of a computer monitor creating someone else’s dream. The person I interacted with most at the office was the evening cleaning lady, Monica. She’d come in around 7 pm for her shift, and because we were usually the only two there by that point, she’d strike up a conversation. She asked if I was married, and I nodded my head yes. Did I have kids? Another nod. What did I do for fun? That one got me thinking. I sat for a moment before telling her about a book I was reading or a project I was working on at the office. Her expression alone was enough to let me know I didn’t have the foggiest idea of what “fun” meant.

Sometimes Monica would show me pictures of her adult children, and as the years progressed, her grandkids, too. There were vacation photos of Monica and her friends, poolside, holding piña coladas at a Caribbean resort; and then there was the Jersey shore house she and her husband saved up to buy.

Then, one night Monica told me she was retiring. I thought, “How can she be retiring? She just started working here!” But she hadn’t just started working there; in fact, years had passed. While I sat, burning the late-night oil at the same desk, with the same job title, and going home to the same apartment, she walked her kids down the aisle, became a grandmother, saw the ocean for the first time, and became a proud homeowner.

It suddenly dawned on me at that very moment that this woman who spoke broken English, didn’t have a high school diploma, and was living paycheck to paycheck, had created a much richer life for herself than I had for myself — with a lot fewer resources.

I had a six-figure job, an assistant with whom I spoke almost exclusively via email (even though she worked mere feet from me), and a standing lunch order at the deli downstairs. I hadn’t seen my friends in ages and when I did, the only news I had to share revolved around work. I, like many others, was so busy exchanging business cards, perfecting my elevator pitch, and updating my LinkedIn profile that I became a walking, talking, breathing resume.

But I don’t want people to remember me by my resume. When my eulogy is read many, many years from now, I want it to reflect a life well-lived. Your eulogy will be about how you made people feel; it will be about the things you did or didn’t do that made you who you were. It will reflect what people miss about you and how you will be remembered; what legacy you leave behind. Chances are, not many of those traits will be found on your resume. Think about it: No one is going to stand up at my funeral and say, “Jenny was a real master at Excel, and I always admired how she completed her LinkedIn profile to 100 percent. She really gave it her all!” So, what will they say?

When I left my corporate job, I left something else behind too. I left behind the notion that my work was my life, and I set out to create a more balanced existence that I could enjoy. Three years ago, I launched my business, Running With Heels, and started living life as if I was crafting my eulogy rather than fine-tuning my resume. In building my company, I didn’t want to just create a job for myself. I wanted to create a community of women who would support one another personally and professionally; a community of women who would have each other’s back. I wanted to show women that we not only can show our true colors, but also that we should.

I also wanted to experience new things and return to some other things I enjoyed in the past, like helping others. I started volunteering for story time at my daughter’s school, and chaperoning class trips. I began working the monthly overnight shift at a local men’s homeless shelter. And, despite my mother’s advice, I began to talk to strangers.

These days, joy is my main driving force. I act silly. I drag my husband to karaoke and insist that we sing our wedding song. I rent Santa Claus costumes for my friends and me and participate in Santacon, the largest Santa meet-up in the world, in NYC. I surprise the school crossing guard on her birthday with a cupcake and candle, and parade down the block singing with my daughter. I say what I think, for better or worse. I create goals that scare the hell of me and then work hard to achieve them. I travel the world when the opportunity arises. I always choose my own adventure. We only have one life to live, and I want to squeeze every last ounce of juice out of it while I can. When I die, I hope my to-do list still has things left on it, but that my bucket list is complete.

It wasn’t easy for me to get to this point, though. It can be overwhelming, but changing your mentality and your actions is doable — and absolutely worth it. Here are five tips that have helped me live a better life — I call them the ABCs for living your best life:

A: Ask. Ask questions; ask for help; ask for advice. Ask others, and ask yourself.

B: Be comfortable being uncomfortable. Getting out of your comfort zone helps you grow as a person. I hate needles, but I give blood every quarter because someone out there needs it. I hated public speaking, but I applied and gave a TED talk last year. I love my 1,000-thread-count bed sheets, but every 30 days I trade them in for a standard-issue cot in a homeless shelter. Technology freaks me out, but I taught myself how to produce a podcast — and despite all my fears, it was awarded “New and Noteworthy” status within the first nine days of launching.

C: Choose your own adventure. Do not lead the life people expect you to; lead the life you want to.

D: Desire overrides fear. Almost everything I’ve ever wanted to do has scared the hell out of me, but I let my desire to do it override my fear and I keep moving forward.  

E: Expect imperfection. If you wait for the perfect time to do something, you’ll never do it. Forget about waiting for everything to be “just right,” and do what you want to do now.  The other day, I heard a quote from one of Canada’s most successful women entrepreneurs, Kelsey Ramsden, that really stuck with me and hopefully it’ll stick with you, too: “Never ready, Set, Go!”

So, whether it’s tonight while brushing your teeth or tomorrow on your morning commute, think about how you want to be remembered, and what actions it will take for you to make that perception a reality.

I hope you live the kind of life that makes you feel truly alive.

Jenny Powers is a member of the DailyWorth Connect program. Read more about the program here.