“In the end, we only regret the chances we didn’t take, the relationships we were afraid to have, and the decisions we waited too long to make.”
— Lewis Carroll
I believed a lie for a long time.
And I’m willing to bet you’ve believed it too.
It goes something like this: “Just put in the work now, sacrifice everything, and someday it’ll all be worth it.”
Not that long ago, I was working in the Silicon Valley startup scene and doing well by every social metric.
I had pre-IPO stock options.
A great salary and bonus structure.
An expense account to entertain clients.
The only problem?
I was stuck in a someday trap.
Someday I’ll take that trip to Costa Rica.
Someday I’ll start that business.
Someday I’ll get back in shape.
But my career was flying high.
Just put in the work now, sacrifice everything, and someday it’ll all be worth it. Right?
The Hidden Cost of Deferred Living
The “someday” mindset is a scam.
Because when we say “someday,” we’re trading real, tangible time today for imaginary time tomorrow.
The conversation you could have with your partner tonight is real. The walk you could take with your dog is real. The vacation you keep postponing is real.
And every missed moment quietly stacks up.
You can’t get those opportunities back later.
The longer we defer living, the more entrenched the habits become — until one day, we become the person who’s always too busy, too tired, too distracted.
Today is your life.
And achieving some shiny milestone “someday” won’t magically undo years of neglect.
It won’t flip a switch that suddenly makes you present, connected, or fulfilled.
Success doesn’t give you your life back. It just gives you more goals to chase.
The goalposts keep moving further out, and you stay on the hamster wheel.
The Difference Between Success and Fulfillment
We love a good success story.
We just conveniently skip the messy parts.
I know seven-figure business owners who:
- Can’t sleep without medication
- Miss most of their kids’ important events
- Haven’t taken an unplugged vacation in years
- Haven’t had a meaningful conversation with their spouse in months
Meanwhile, their LinkedIn and Instagram feeds?
Full of humblebrags, thought leadership, and professional accolades.
And that’s the whole con. We believe success leads to fulfillment.
But often, the very path to success destroys the sources of true fulfillment along the way.
I’ve Tried It Both Ways
In my professional life and the earlier years of my business, I lived the someday plan.
I worked long hours.
I ignored the most important people in my life more than I care to admit.
I let friendships slide.
I skipped workouts.
And I told myself it would all be worth it.
Someday.
Then I started hitting financial goals that felt like important benchmarks.
And absolutely nothing changed.
I just invented new reasons to keep sacrificing.
It wasn’t until the last few years that I made a hard shift.
Now, I’m ruthless about commitments that bring me fulfillment.
I’m done working by 3:30 most days.
I walk every day, sometimes multiple times per day.
I take the dogs to the river.
I exercise when I have the energy for it.
I have dinners with my wife every night.
I read more for fun.
I travel to places that inspire me.
And ironically?
I feel more energized, more creative, and more enthusiastic about my work than ever before.
Because I’m not just working toward a life.
I’m actually living it …right now.
Breaking the Cycle
If you’re living the “someday” plan, here are a few ideas to shift:
Define your “enough.”
Get painfully clear on what you actually need to support your ideal life — not what society tells you to chase. You might be surprised what you can live without.
Schedule life before work.
Plan your vacations, date nights, hikes, and workout time first.
Work fills the space you give it — so give it less.
Create a “Not Someday” list.
Write down the experiences you refuse to delay. Then commit to doing one every month or quarter, even when life gets busy (especially when life gets busy).
The Cruel Truth
“Someday” is a moving target.
It’s a mirage that keeps you sprinting.
It’s an excuse for not showing up — for yourself, and for the people you love — today.
I’m not saying don’t work hard. I’m not saying don’t stretch yourself.
I’m saying your ambition deserves to be applied to your whole life, not just your professional and business goals.
Because the cruel truth?
Nothing is more expensive than regret.
Today is all we’re guaranteed.
Let’s live like it.
Live bravely,
Michael
