I’ve been thinking a lot lately about people who build things.
Not just companies.
Lives.
There’s something fascinating about driving past a small business and realizing that, at some point, somebody decided to bet on an idea.
The restaurant you love.
The farm you visit on a Saturday morning.
The little shop that somehow became a local institution.
The contractor whose name seems to be on every truck in town.
The business that started at someone’s kitchen table and now employs 30 people.
We see the finished version.
What we rarely see is the decision that came before it.
Was there a corporate job they couldn’t do anymore?
An idea scribbled somewhere that wouldn’t leave them alone?
A family business they inherited but weren’t sure they wanted?
A moment when someone looked at their spouse and said:
I think I’m actually going to try this.
And then there’s the question I’m even more interested in:
Did building the business give them the life they thought it would?
The Story We Tell About Building Something
We tend to romanticize entrepreneurship.
Freedom.
Flexibility.
Being your own boss.
Building something that belongs to you.
And sometimes, I’m sure, it is all of those things.
But building something also comes with trade-offs.
Payroll, risk, customers, employees depending on you and weekends that aren’t really weekends.
The inability to completely switch off because, ultimately, the buck stops with you.
And perhaps the uncomfortable realization that sometimes escaping one version of the grind simply means you’ve created another.
Which makes me wonder:
What are we actually trying to build?
Because a bigger business isn’t necessarily a better business.
Just as a bigger title isn’t necessarily a better career.
More revenue doesn’t automatically mean more freedom.
More responsibility doesn’t automatically mean more meaning.
And growth, despite how often we celebrate it, isn’t always the right measure.
That feels worth exploring.
THE WIDER QUESTION
What are you actually
trying to build?
Not what are you trying to grow.
What are you trying to make possible?
There’s Usually a Measure Underneath the Measure
This is something I keep coming back to with The Wider Measure.
Most of us have visible measures of success whether it’s revenue, promotions, followers, customers, headcount, square footage, or growth.
They’re easy to see and even easier to compare.
But underneath those measures are usually the things we were hoping they would give us. Things like security, freedom, time, pride, autonomy, and impact.
A sense that the work we're doing matters.
Maybe even the ability to pick our kids up from school on a Tuesday afternoon.
The visible measure is often just a proxy for the thing we actually want.
And that distinction matters.
Because it’s entirely possible to succeed by the first measure while quietly losing by the second.
Introducing: Built Differently
So I want to try something new.
Over the next several months, I’m going to start sitting down with people who have built businesses of their own.
Some will be small.
Some may not be anymore.
Some will have left successful corporate careers.
Others may have never wanted one.
Some will be aggressively growing.
Others will have made the very deliberate decision not to.
I want to understand the decisions underneath the businesses.
The risks.
The trade-offs.
The leadership lessons.
The moments they nearly quit.
The things that worked.
The things that absolutely didn’t.
What happened when their business outgrew them.
What they wish they’d known before they started.
And what success looks like from the inside, once you’re the person responsible for making the whole thing work.
I’m calling the series:
Built Differently
A Wider Measure series about people building businesses — and lives — on their own terms.
But this won’t really be a series about entrepreneurship.
At least, I don’t think it will. It will be a series about choices.
Because building a business forces you to make them.
What gets your time? How much is enough?
What are you willing to sacrifice? What aren't you?
When do you keep pushing? When do you stop growing?
Who do you want to become while you're building it?
Those aren't exclusively business questions.
They're life questions.
The Questions I Want to Ask
There are a handful of questions I plan to ask every person I interview.
What does success mean to you today that it didn’t five years ago?
What have you deliberately chosen not to optimize?
What’s a trade-off you’ve made that people looking from the outside probably don’t see?
What are you building beyond the business?
But there’s one question I’m particularly interested in.
One I suspect could produce very different answers depending on who is sitting across from me.
By what measure will you know this was worth it?
Not successful. Worth it.
Because those are two very different questions.
A business can be financially successful and cost someone their marriage.
A career can be objectively impressive and leave someone wondering where a decade went.
A company can grow rapidly while its founder quietly wishes they could return to the version they had three years earlier.
And the opposite can be true, too.
Someone can run a business that will never make a national headline and create meaningful work for 15 people, be home for dinner most nights, know half the community by name and genuinely love Monday morning.
Who gets to decide which one is more successful?
That's the whole point.
You do.
Maybe the goal isn’t to build bigger
We live in a culture that loves scale.
If something works, grow it.
If you have an audience, make it bigger.
If you have a business, add locations.
If you have a good career, get the next title.
If you earn enough, earn more.
There's nothing inherently wrong with any of that.
Ambition can be wonderful.
Growth can create opportunity, impact and wealth.
But growth without intention has a funny way of becoming its own objective.
And eventually we can find ourselves working incredibly hard to maintain something we never consciously decided we wanted.
Maybe the more interesting question isn't: How big can I make this?
Maybe it's: What am I trying to make possible?
More time?
More impact?
Financial independence?
Creative freedom?
Something meaningful to hand to the next generation?
A team you’re proud to lead?
A life that feels like yours?
Once you know that, you can choose the measures that actually matter.
And sometimes that will mean going bigger.
Sometimes it might mean staying exactly where you are.
That’s what I want to explore with Built Differently.
Not a formula for success.
A collection of honest stories about what success actually looks like when you're the one living it.
I need your help
I have a few people in mind for these conversations.
But I know there are extraordinary stories hiding in businesses I’ve never heard of.
So I want your nominations.
Maybe it's someone who walked away from a completely different career and started over.
Someone running a second- or third-generation family business.
Someone who built something from their kitchen table.
Someone whose business almost failed — and came back.
Someone who intentionally keeps their company small.
Someone quietly employing dozens of people without ever appearing on a “30 Under 30” list.
Or simply someone whose approach to business, leadership or life has made you think:
They're doing something differently.
Send them my way or feel free to nominate here →
Because I have a feeling that if we sit down with enough people who have chosen to build differently, we'll start to see some patterns.
Not just about how to build better businesses.
But about how to build better lives.
And maybe, somewhere in their answers, we'll get a little clearer about our own.
So I'll leave you with the question I'll be asking them:
By what measure will you know this was worth it?
Until next time,
Nikki
The Wider Measure