When to Dig In, and When It’s Just a Wall

~by Haley Lynn Gray~

If there’s one thing I’ve learned, it’s that perseverance pays off. I’m probably the poster child for sticking with something — I once sold a dining room full of watermelons, and I finished an MBA while my life was on fire.

It’s also true that perseverance is sometimes indistinguishable from beating your head against a wall. Knowing which one you’re doing is the actual skill.

What sticking with it buys you

You finish things. Most goals aren’t lost to a dramatic failure; they’re abandoned quietly at the point where they stopped being fun. The people who reach them aren’t necessarily more talented — they were still there.

People notice. Reliability compounds. Being someone who doesn’t give up when a project turns difficult is a reputation you can only build slowly, and it brings opportunities that never get advertised.

It teaches you what you can survive. Every hard thing you finish lowers your estimate of how frightening the next one is.

The part nobody says out loud

Tenacity has a shadow, and it’s expensive: persisting at something that isn’t going to work.

The same instinct that gets you through a difficult year on a good idea will keep you going for three years on a bad one. Sunk cost feels like commitment from the inside.

A real problem-solver knows when to dig in — and when to admit the approach has failed. They know when to ask questions, and they also know when the source of information has been exhausted and it’s time to find another route entirely.

How to tell which one you’re in

Is it getting harder or easier? Genuine progress usually shows some sign of movement, even slow. If every month costs more than the last and delivers less, that’s information.

What have you learned recently? Productive persistence teaches you something each cycle. Unproductive persistence is the same failure repeated with more effort.

Would you start it today? Knowing what you now know, with no money or time already spent — would you begin? If not, you’re continuing out of history rather than judgement.

Have you changed the approach, or just the intensity? Trying harder at something that isn’t working is not a strategy. Change one thing and test again.

What would you tell a friend? We’re all far clearer about other people’s sunk costs than our own.

Quitting well

Stopping isn’t failure. Stopping late is expensive; stopping deliberately is a decision like any other.

Take what you learned, be clear about why you’re stopping, tell whoever needs to know, and put the energy somewhere it can compound. Ending something frees capacity for the thing that will work.

The short version

Dig in. Stay when it’s hard, because almost everything worthwhile has a stretch that feels awful in the middle.

Just check, occasionally, that you’re persisting towards something rather than simply persisting. The wall doesn’t care how determined you are.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

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