No More Somedays: Living With Fewer Regrets
Imagine you’re 80 years old, sitting quietly in your favorite chair, reflecting on your life.
What will you smile about?
And what will you wish you’d done differently?
When people are asked, near the end of their lives, about their regrets, the answers aren’t about money or titles or promotions. They’re about freedom, courage, connection, and purpose.
These are powerful reminders for how we live today. So let’s take a closer look at what people actually regret, and how you can choose differently, while you still can.
The 5 Most Common Regrets of the Dying
These insights come from Bronnie Ware, a palliative care nurse who spent years documenting what her patients told her in their final weeks. The regrets she heard most often weren’t about what people did, they were about what they didn’t do.
Here are the five that came up again and again:
1. “I wish I’d had the courage to live a life true to myself.”
So many people realize too late that they lived according to other people’s expectations. They followed the path that seemed safe or acceptable, not the one that felt right.
Lesson: If something inside you is whispering that there’s more out there for you…listen! Whether it’s changing careers, working remotely, moving abroad, or starting that passion project, the time to explore it isn’t “someday.” It’s now.
2. “I wish I hadn’t worked so hard.”
People don’t regret effort, they regret exhaustion. The missed birthdays, forgotten dreams, the years that passed in a blur.
Lesson: Work will always expand to fill your time if you let it. It’s up to you to create boundaries. Choose work that gives you time back. Choose goals that include living, not just earning.
3. “I wish I’d had the courage to express my feelings.”
So many people suppress their voice, whether it’s at work, at home, or with friends. They avoid conflict, they people-please, or they stay quiet because it feels safer.
Lesson: Speaking up is vulnerable. But it’s also powerful. Whether it’s asking for flexibility at work, standing up for what you want, or telling someone you care about them, your voice matters.
4. “I wish I had stayed in touch with my friends.”
As life speeds up, relationships can fall to the side. We assume we’ll always have time to reconnect “later.” But time doesn’t always wait.
Lesson: Make the call. Send the message. Book the trip. Don’t let your ambition come at the cost of your connection.
5. “I wish I had let myself be happier.”
This one hits hard. People realized, albeit too late, that happiness is a choice. They’d been waiting for permission to enjoy their life, but it never came.
Lesson: You don’t have to “earn” happiness. You can choose joy, presence, and gratitude right now, even in small ways. Don't delay it.
Pause and Reflect
Take a moment and ask yourself:
Am I living in alignment with what I truly want?
Am I prioritizing people and experiences over achievements and appearances?
Am I making time for joy, not just tasks?
Your answers aren’t set in stone. And they’re not about judgment. They’re a starting point.
What This Means for Today
There’s no such thing as a perfect path. But there is such a thing as an intentional one.
If you're reading this, there’s a good chance you’re already thinking differently about life and work. You want more than a paycheck. You want freedom. Flexibility. Fulfillment.
That’s a legitimate goal. One that takes effort, strategy, and yes, support.
So remember:
Don’t put off the life you’re meant to live.
Don’t wait for the “right” time.
Don’t let fear disguise itself as practicality.
The Quiet Revolution
What we’re seeing in the remote work movement isn’t just about location. It’s about agency. People are realizing they don’t have to accept the default.
They can design a career around their values.
They can build income without sacrificing joy.
They can live more consciously, more creatively, and more courageously.
That’s we stand for. And we’re honored to be part of this quiet revolution.
Final Thoughts
You still have time.
To choose.
To change.
To create a life you won’t regret.
If you’re feeling called to explore new ways of working, living, and leading, then follow that call.
And if you want help figuring out the next steps, we’re here when you’re ready.
See how The Remote Job Academy can support you in living a life with more freedom and flexibility!
Stay Rebellious,
Michelle
This week’s article is sponsored by Tulsa Remote. Tulsa Remote is redefining what’s possible for remote workers by offering top talent the chance to thrive in a vibrant, welcoming community, without sacrificing career ambition. Through relocation incentives, community programming, and professional support, Tulsa Remote helps individuals build meaningful lives in a city that values connection and innovation. Remote work has changed the where, Tulsa Remote is changing the how.