April 26, 2025

“Someday” is a dangerous lie.

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I believed a lie for a long time. And I 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.

A few weeks ago, I had coffee with a friend who's crushing it by every business metric. His SaaS business crossed $5M ARR with ten employees, he’s been featured in Fast Company, and his board is thrilled. An entrepreneur’s dream, right?

But midway through our conversation, sharing the less-sexy details of his story, this guy got physically upset in a crowded coffee shop.

"I've been saying 'someday' for seven years,” he told me. “Someday I'll take that trip with my wife. Someday I'll be at my kid's events. Someday I'll get back in shape."

But it turns out his somedays are taking too long. And life outside of work is at a breaking point.

His marriage is not going well. He’s out of touch with his kids. And his doctor just prescribed blood pressure medication.

Meanwhile, business is booming.

Just put in the work now, sacrifice everything, and someday it'll all be worth it.

The Cruel Math of Deferred Living

The "someday" mindset is a scam.

Because when we say "someday," we really mean we’re trading guaranteed time today for imaginary time in the future.

But the time you could spend talking to your kids tonight is real. Not walking your dog is real, poor little guy. Those trips you're skipping are real. The conversations you're not having with your partner at dinner are very real. And adding up.

We can’t get those opportunities back later.

And the perpetual habit of trading now for later adds up to the person you are. Today. Because today is your life. It’s all we can be sure of, here and now.

And despite wishful thinking, you won’t change who you’ve become by achieving a milestone “someday.” People don’t cross net worth goals and stop looking at their phones obsessively. They don’t see certain numbers and suddenly start connecting with their neglected spouses. And the kids don’t just say, “Hey Dad, we’re so glad you’re back.”

That’s not how life works.

The free time you expect “someday” doesn't exist now, and evidence suggests it probably never will. Because people hit their "someday" numbers and roll straight into new goals.

The goalposts keep sprinting away, and life goes on as usual.

A Closer Look At “Success”

We look at people who've "made it" and conveniently ignore how miserable many of them are. Smiling faces painted on.

I know seven-figure business owners who:

  • Can't sleep without medication
  • Miss their kids' events on the regular
  • Haven't taken an unplugged vacation in years
  • Haven't had a real conversation with their spouses in months

Meanwhile, their social media feeds are full of humblebrags and poetic advice.

And that's the whole con. We believe success leads to happiness. But in reality, the path to success often destroys the things that actually create happiness.

I Tried It Both Ways

For the first several years of my business, I lived on the someday plan.

I worked long days, ignored my wife more than I’d like to admit, let friendships fade, and told myself it would all be worth it...someday.

Then I hit my first “someday” revenue goal. And absolutely nothing changed. I just found new reasons to keep sacrificing. But in the last couple of years, I've committed to doing things differently.

I’m very cautious about commitments. I want as few as possible. I limit my work hours. I take long walks without my phone. I take Fridays off, minus one hour. I have dinner with my wife every night, no phones at the table. I’m more social than ever. I’m reading non-business books. I’m taking actual vacations.

And the outcome is that I feel more creative and have more enthusiasm for my work. I feel like I’m actually experiencing life instead of just working through it.

Breaking the Someday Cycle

If this issue is resonating because you're living the "someday" life, here are a few tips that might help:

  1. Start by defining your enough: Figure out the actual amount of money that supports your ideal lifestyle. Not society's number. Your number, where you can rest easy and live life.
  2. Schedule your life first, then work: Plan your vacations, date nights, and personal time before you decide to cram your calendar with work. Life first, business second. Then stick to the plan.
  3. Create a "not someday" list: Write down experiences that you refuse to put off. Then schedule one of them every month, regardless of how busy you think you are.

The Bottom Line

Someday is a goalpost that will keep moving as you inch closer. And it’s an excuse for not showing up today. For yourself, and for the people in your life.

The only day we're guaranteed is today, and trading too many todays for somedays is a terrible habit.

I'm not suggesting being lazy or quitting what you’re working on. And I’m not saying you don’t have to make sacrifices sometimes. There has to be a balance, of course.

I'm suggesting you apply your ambition to your whole life, not just your business.

Because the notion of “someday” will keep you on the hamster wheel forever. And nothing is more expensive than regret.

Today, we get the chance to live our lives. Right now.

Will there be trade-offs and hard work involved in building something meaningful? Of course. But those trade-offs should not destroy our lives in the short term.

And the life we have today is all we can be sure of.

That’s all for this week.

See you next Saturday.

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