Pick One Challenge

A woman writing in a notebook

~by Haley Lynn Gray~

People ask me almost daily how I get so much done, and whether I actually sleep. I do, and quite well.

What I think makes the difference isn’t energy. It’s that I pick a challenge and commit to it — one at a time, deliberately, and see it through.

Mine have included getting into Duke, finishing the MBA while everything else was on fire, building businesses, and a considerable amount of what happened in between.

One, not five

The word that matters is one.

The commonest failure I see in ambitious people isn’t laziness — it’s five simultaneous projects, each getting a fifth of the attention, none finishing. It feels productive and produces almost nothing.

A single challenge, properly chosen, gets your best hours and your best thinking. And finishing changes something: every hard thing you complete lowers your estimate of how frightening the next one is.

How to pick one worth doing

It should slightly frighten you. If you’re certain of the outcome, it’s a task rather than a challenge.

It should be finishable. A goal with an end. “Grow the business” never completes; “add twelve retainer clients by December” does.

It should be yours. Not the thing you think you ought to want. The work you’re genuinely drawn to is where your best output lives, and a challenge you picked out of duty will lose to anything urgent.

And you should be able to name what changes when it’s done. If you can’t, it may not be worth the year.

Then make it survive ordinary life

Tell someone. A private goal is easy to quietly abandon.

Put the work in the calendar. A challenge with no scheduled time is a wish.

Decide what gives way. Taking something on means something else gets less — choose it deliberately rather than discovering later that it was sleep.

And expect the middle to be unpleasant. Every worthwhile project has a stretch where the novelty has gone and the end isn’t visible. That’s not a sign you chose wrongly; it’s simply where most people stop.

The honest caveat

Persistence pointed at the wrong thing is expensive. Check occasionally that you’d still start this today, knowing what you now know.

But if the answer is yes, keep going — and don’t add a second challenge until the first one is finished.

What’s yours at the moment?

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.

Related Posts

Traumatic Brain Injury: The Ugly, the Bad & the Good

Traumatic Brain Injury: The Ugly, the Bad & the Good

It’s been almost a year since I sustained a traumatic brain injury after falling off of a horse. I landed directly onto my head, which resulted in a disproportionately bad injury and permanent brain damage. With this kind of injury comes a variety of symptoms and complications that must be dealt with on a daily basis as one’s brain heals.

Entrepreneur Interview – Zerah Capili

Entrepreneur Interview – Zerah Capili

Zerah Capili works as a Creative Coordinator for Hope for the Heart and Soul Foundation, a NGO-based company that introduces underprivileged children to arts and crafts. She also handles her own business called “Sapinsapin Tanzan”, which sells mostly handmade products and features different quirky knick-knacks.

My Lesson in Tactical Manipulation and Self Worth

My Lesson in Tactical Manipulation and Self Worth

He said the words. The ones designed to hit at the heart of my self-worth. “You aren’t worth what I’m paying you.” I felt like a cartoon character that had all of the oxygen sucked out of the room.

How to Gain Control of Your Thoughts

How to Gain Control of Your Thoughts

Like many others, I had to learn how to gain control of my thoughts. Giving up sarcasm was huge. I had to come up with a new approach to humor. How could I be funny without being negative?

Find what you need

Lead Your Team

Delegation, hiring, difficult conversations, and becoming the boss you'd want to work for.

Build the Business

Pricing, launching, systems, and building something that doesn't depend on you.

Women in Leadership

Negotiation, the pay gap, and what the research actually says about women who lead.

Get Seen

Being visible without the cringe — podcasts, content, and being remembered.

Lead Yourself

Courage, your inner critic, time, and protecting what matters most.

You're Not Alone

The loneliness of leading, and why the best owners don't solve everything alone.