We all know we’re going to die. It’s the one thing everyone has in common, yet it’s the one thing we spend our entire lives trying to ignore. We chase the next promotion, the bigger house, or the perfect Instagram feed, all while pushing the things that actually matter to some mythical “later.”
But, just like Lady Gaga and Bruno Mars sings, “Nobody’s promised tomorrow”.
The difference between living a life of fulfillment and a life of quiet desperation isn’t luck or money. It’s perspective. Specifically, it’s the ability to bring your future regrets into the present so you can do something about them today.
The Deathbed Thought Experiment
I want you to try something. Close your eyes and imagine you’re in your deathbed right now. The race is over. You aren’t worried about your inbox, your networth, or what your neighbors think of your Tesla.
In that moment of total clarity, what are the five things you’d regret most?
For most people, they look a lot like this:
- “I wish I’d spent more time with the people I love.” We trade our kids’ childhoods or our parents’ final years for “busy-ness.”
- “I wish I’d gone on that dream vacation.” We wait for the “right time” to travel, but the right time is usually whenever you’re still healthy enough to enjoy it.
- “I wish I’d picked up that hobby or skill.” Whether it’s playing pickleball, learning to code, or painting, we let “I’m not good at it” stop us from even trying.
- “I wish I’d taken more risks.” We choose comfort over growth and wonder “what if” for decades.
- “I wish I’d been truer to myself.” Living the life others expected of us instead of the one we actually wanted.
Designing Your Life Around Your Regrets
Once you’ve identified your “Big Five,” the next step isn’t just to feel bad about them. It’s to design your life so they never happen.
If your regret is “not enough family time,” you don’t just “try to be home more.” You schedule it. You treat a Tuesday night dinner with your spouse with the same level of importance as a major work presentation.
If it’s that dream vacation, you don’t wait for a windfall. You set up a dedicated “Experience Fund” and automate a transfer every payday—even if it’s just $500.
The goal is to stop reacting to life and start architecting it.
Making the New Habits Stick
Identifying what matters is easy. Actually changing your behavior? That’s where most people fail. We make resolutions, hit it hard for three days, and then slip back into the “busy” trap.
If you want these new life-design habits to last, you need a system:
- Start Stupidly Small: If you want to learn a new skill, don’t commit to an hour a day. Commit to 5 minutes. It’s impossible to fail at 5 minutes. James Clear calls them atomic habits.
- Audit Your Time: We all say we don’t have time, but we all have 24 hours. Check your screen time. If you’re spending two hours a day on TikTok but “can’t find time” for your family, you don’t have a time problem; you have a priority problem.
- Environment Design: If you want to practice that hobby, put the tools in plain sight. If the pickleball racquet is in its case in the storeroom, you’ll never play it. If it’s on a stand in the living room, you will.
- The Weekly Review: Every Sunday, look at your calendar. Ask yourself: “Does this week reflect my Big Five regrets, or am I just filling time?”
The truth is, dying with no regrets isn’t about doing everything. It’s about doing the right things. Bring your deathbed perspective into your Monday morning, and watch how quickly your life changes.
Stop waiting for “later.” Later is a trap. Start today.