How Do You Know When You’ve Tried Hard Enough?

I was cleaning out the ice cream shop when I had the thought.

Maybe I didn’t try hard enough.

It was fleeting.

Just one of those shitty little thoughts that slips in before the rational part of your brain has time to intercept it.

Maybe I could have marketed it better.

Maybe I could have done more events.

Maybe I should have been there more.

Maybe I could have figured out how to make the numbers work.

Maybe I gave up too soon.

And here’s the irritating part:

I probably could have tried harder.

That’s what makes this question so difficult.

There Is Always Harder

I could have worked another shift.

I could have run another promotion.

I could have spent more money.

I could have stayed open another summer.

I could have posted more.

I could have created another event.

I could have gotten up earlier, stayed later, thought about it longer and thrown another piece of myself at the problem.

There was absolutely more I could have done.

There almost always is.

That’s the problem with asking:

Did I try hard enough?

It’s an impossible question to answer because there is no objective finish line for effort.

How do you know when you’ve officially done everything?

You don’t.

There is always another strategy.

Another conversation.

Another month.

Another dollar.

Another hour.

Another attempt.

Another Monday.

There is always harder.

And I’m starting to think that’s exactly why Could I have tried harder? is the wrong question.

I’ve Been Asking Myself This Question My Whole Life

The ice cream shop isn’t the first place I’ve done this.

Not even close.

I’ve done it with businesses.

I’ve done it with money.

I’ve done it with productivity.

I’ve done it with my body for more than 30 years.

If losing weight wasn’t working, I assumed I wasn’t trying hard enough.

Eat less.

Exercise more.

Be more disciplined.

Track everything.

Try another program.

Start again Monday.

It never occurred to me that the amount of effort required might actually be useful information.

I thought effort was evidence of character.

Hard meant I cared.

Hard meant I was committed.

Hard meant I wasn’t a quitter.

And if hard wasn’t working?

Obviously, the answer was harder.

I’ve gotten very good at harder.

But Harder Has a Price

This is the part I didn’t understand for a long time.

Every additional unit of effort costs something.

I think about my life in what I call the Four Currencies:

Time. Energy. Attention. Money.

Those are the resources we actually have to spend.

And every time I say, I could try a little harder, I’m agreeing to spend some combination of them.

Another summer at the ice cream shop isn’t just another summer.

It’s hours time I don’t get to spend with my kids.

It’s the energy required to manage it.

It’s the attention it occupies even when I’m not physically there.

It’s money I might need to put back into the business.

It’s also whatever I can’t spend those currencies on because they’re already committed.

That’s the part we tend to leave out of the equation.

We ask:

Could I keep going?

Of course I could.

I’m very good at keeping going.

The better question is:

What will keeping going cost me?

And do I still want what I’m buying?

We Don’t Ask Ourselves What We Want

There’s another question buried underneath all of this that I’m realizing I don’t ask myself nearly enough.

What do I want?

Not what makes the most sense.

Not what I should do.

Not what would prove I can do it.

Not what everyone else needs from me.

Not what I’ve already invested too much time or money into to walk away from.

What do I actually want?

Even writing that feels a little indulgent.

Because somewhere along the way, wanting became something we were supposed to be suspicious of.

How many times have we heard:

You don’t always get what you want.

Of course we don’t.

That’s objectively true.

But I think some of us heard that so many times we accidentally translated it into:

What you want isn’t particularly important.

Wanting something isn’t responsible enough.

It isn’t practical enough.

It isn’t a good enough reason.

You can’t close a business because you don’t want to own it anymore.

You need spreadsheets.

You need declining revenue.

You need exhaustion.

You need some circumstance beyond your control that grants you permission.

You need a reason everyone else will accept.

Apparently, I don’t want this anymore doesn’t count.

And on the other side, I want this can feel just as uncomfortable.

I want more freedom.

I want more money.

I want to travel.

I want work I enjoy.

I want my body to feel good.

I want an easier life.

I want something different.

Okay, but why?

What’s the plan?

Have you earned it?

Is it realistic?

What about everyone else?

We require wanting to present a very convincing case before we’re willing to take it seriously.

I’m not suggesting we should get everything we want.

Obviously.

I’m suggesting maybe we’re allowed to want it anyway.

Wanting isn’t a guarantee.

It’s information.

And if I’m going to decide whether something deserves more of my time, energy, attention and money, maybe what I actually want should get a seat at the table.

Not the only seat.

But a fucking seat.

Can I Make It Work Is Not the Same as Do I Want to Make It Work

This distinction has been a big one for me.

Could I have found a way to keep the ice cream shop open?

Probably.

That doesn’t mean I wanted to.

And that doesn’t mean I should have.

Those are three completely different questions.

I think a lot of us stay in things because we confuse our ability to endure them with evidence that they’re worth enduring.

Businesses.

Jobs.

Commitments.

Projects.

Habits.

Maybe even versions of ourselves we’ve simply outgrown.

We know we can keep going.

So we assume we should.

And we become so busy figuring out whether we can make something work that we forget to ask whether we still want it to.

Maybe that’s the question I’ve been skipping.

Not:

Could I try harder?

But:

If I try harder and it works, do I actually want the life on the other side?

What If the Amount of Effort Is Information?

My experience losing weight recently forced me to look at this differently.

I spent more than 30 years trying to manage my weight.

I tried harder approximately 4,000 different ways.

Then I started using a GLP-1 after more than 30 years of struggling with my weight.

And something that had required an extraordinary amount of my time, energy and attention became dramatically easier.

That experience messed with my head a little.

Because if something could become easier simply because I had a better tool, what did that say about all those years I’d interpreted difficulty as a personal failure?

Maybe difficulty wasn’t proof that I needed to try harder.

Maybe it was information.

Maybe the system wasn’t working.

Maybe the tool wasn’t right.

Maybe the economics didn’t make sense.

Maybe my body needed something different.

Maybe the season had changed.

Maybe I had changed.

Maybe something could be possible and still not be worth what it required from me.

That’s a very different way to look at effort.

So How Do You Know When You’ve Tried Hard Enough?

I wish there were a formula.

Believe me, I would love a spreadsheet that said:

Congratulations! You have now tried 87.3% hard enough. You may quit without guilt.

Unfortunately, I have yet to find one.

But I’m starting to ask myself better questions.

Not:

Have I tried everything?

Because I never will.

Instead:

Do I still want what I’m working this hard to get?

Not the version I wanted three years ago.

Do I want it now?

Is my effort creating meaningful progress, or mostly creating more effort?

Am I actually moving something forward, or have I become extremely efficient at struggling?

What is this costing me in my Four Currencies?

How much time?

How much energy?

How much attention?

How much money?

And perhaps more importantly, what am I not doing with those currencies because they’re tied up here?

If nothing changed for another year, would I willingly keep paying this price?

That’s a particularly clarifying one.

If the business stayed exactly as it is…

If the job stayed exactly as it is…

If the project stayed exactly as it is…

Would I choose another year?

And then there’s the question I probably need most:

Am I continuing because I still believe in where I’m going, or because stopping would make me feel like I failed?

Oof.

Sometimes Stopping Is the More Difficult Choice

I’ve always admired perseverance.

I still do.

Some things absolutely require us to stay when it’s hard.

Building anything meaningful involves periods when the effort doesn’t seem proportional to the result.

Relationships have hard seasons.

Businesses have hard seasons.

Bodies have hard seasons.

Life has hard seasons.

I don’t want to turn harder isn’t automatically better into quit anything that becomes inconvenient.

That’s not what I’m saying.

I’m saying perseverance and self-abandonment can look remarkably similar from the outside.

Only you know what you’re spending to stay.

And sometimes continuing is actually the easier choice.

Continuing means you don’t have to explain yourself.

You don’t have to disappoint anyone.

You don’t have to admit something didn’t turn out the way you expected.

You don’t have to figure out what comes next.

You just keep doing what you’ve been doing.

Stopping asks something different of you.

It asks you to accept that something can have mattered deeply and still be over.

I Didn’t Fail at the Ice Cream Shop

I’m still practicing this sentence.

Closing Creekside doesn’t mean I couldn’t have made it work.

Maybe I could have.

I’ll never know.

That’s uncomfortable for someone like me.

I like knowing.

I like figuring shit out.

I especially like proving that I can.

But I don’t have to exhaust every possible option before I’m allowed to decide I’m done.

I don’t have to spend every remaining dollar.

I don’t have to use every ounce of energy.

I don’t have to give it every hour I have.

I don’t have to reach some mythical point of complete depletion before I’ve officially earned the right to stop.

Maybe I tried hard enough because I decided the additional effort wasn’t worth what it would cost me.

That’s allowed to be enough.

There Will Always Be Something Else I Could Have Done

I think that’s the part I’m finally accepting.

There will always be another thing.

Another promotion I could have run.

Another diet I could have tried.

Another hour I could have worked.

Another way I could have optimized.

Another piece of myself I could have thrown at the problem.

There is always harder.

So maybe I’ve tried hard enough when I’m no longer trying because I believe in where I’m going.

I’m trying because I need to prove I could have gotten there.

That’s a very different kind of effort.

For most of my life, I’ve treated endurance like evidence of character.

Stay longer.

Work harder.

Give it another chance.

Don’t quit.

But I’m beginning to think knowing when to stop requires just as much courage as knowing when to keep going.

Maybe more.

Because “hard enough” isn’t the moment when there is nothing left I could give.

There will always be something left.

Maybe it’s the moment when I decide I’m no longer willing to give what’s left for what I’m getting in return.

I’m not learning how to try harder in this season of my life.

I’ve got that shit down.

I’m learning that harder isn’t automatically better.

And strangely enough, that might be one of the hardest things I’ve ever had to learn.