#70: Go From “If Only” to “What If”?

newsletter Oct 05, 2026

Read This If You Know Life Could Look Different

One reason I started Try Life On was to show examples of what is possible, especially in the realm of designed living.

Not extraordinary people with access to resources we don't have. People with jobs, families, bills, responsibilities, careers. Same considerations making us wonder whether changing life is actually realistic.

There are people all over the world making those shifts.

Sometimes they build financial independence over a decade. Sometimes they move to another country. Sometimes negotiate a different relationship with work. Sometimes start something on the side while keeping their job. Sometimes that little thing becomes much larger.

There isn't one formula because the objective isn't entrepreneurship. The objective is designing a life that makes sense to you.

 

Grayson and Marie: A great example

My conversation with Grayson Hogard, co-founder of Grove Cookie Company with his wife, Marie, is one of my favorite examples.

Grayson spent 14 years working in logistics at Bonneville Power Administration, part of the U.S. Department of Energy. Marie had a corporate career of her own. During the pandemic, Marie started baking at home because she wanted something else to do.

Cupcakes became cookies. Eventually they decided to put the cookies on Instagram and see if anyone would buy them.

That's where I want you to pay attention.

They didn't know where it was going.

They simply moved from “If Only” to “What If.”

Listen to the podcast: [LINK]

Watch the conversation on YouTube: [LINK]

 

The Grove Cookie Company Story

What happened next wasn't part of some master plan.

Grayson's mom bought their first box of cookies. Shortly afterward, a financial advisor asked if they could ship cookies to his clients. That opportunity introduced them to corporate gifting, which eventually became the primary direction of the business.

All the while, they were still working.

As business grew new questions appeared. How do we ship this many cookies? How do we move out of our townhouse and into a commercial facility? How do we hire people? How do we create processes so the business doesn't require us to personally do everything?

They didn't answer those questions before starting. They answered them as they arrived at each step.

Eventually Grove Cookie Company grew into a high six-figure business with five employees. Grayson reached a point where he could leave the government career he'd held for 14 years. When we recorded the podcast his team was at the bakery making and shipping cookies while he was home with his one-year-old son.

The business grew, yes. But pay attention to what else grew with it.

Their options grew. Confidence grew. Relationships grew. Their ability to make decisions about how they wanted to spend their time grew.

That's the part I care about.

 

The Try Life On Principles Inside Their Story

Listening to Grayson and Marie's journey you'll hear Try Life On Principles everywhere:

Employment is not a destination. It's a resource to build life. Grayson used the income and stability of his government career while they built Grove, but he also used what he had learned there. His background in logistics became directly applicable to shipping, warehousing and designing the production flow of their bakery.

Go from “If Only” to “What If.” They didn't begin by trying to replace their salaries. They asked a much smaller question of “...what if we put these cookies on Instagram and see if somebody buys them”? One small experiment created info they couldn't have obtained by thinking about it.

Live life, then figure out the details. They didn't know how to build a commercial bakery when they started because they didn't need to know yet. When the business reached that point they figured it out.

Find the “Who” versus studying the “What” forever. They used a business coach. When Grayson needed to understand requirements for the bakery, he asked someone from the Oregon Department of Agriculture who already understood them. They didn't need to personally know everything, rather, access to people who already did.

Just do and course correct along the way. They thought they were building a consumer cookie business. Corporate gifting appeared and they followed opportunity. Business revealed itself through movement.

Reality is negotiable. Grayson told me he never expected to leave his government career. He had been there for 14 years and expected to continue building his career there. Today that isn't his reality anymore.

 

The Part That Matters

I don't want you to walk away from this thinking you need to quit your job and become an entrepreneur. That misses the point.

Grayson and Marie could have built a smaller version of Grove and continued working their traditional jobs. They could have decided they loved baking cookies from home and kept it there. Their version grew into something larger because that was the path they chose as opportunities presented themselves.

Try Life On isn't a prescribed destination.

It's the practice of becoming intentional about your life and being willing to experiment with what else might be possible.

Your current job might be part of that. Your spouse might be part of it. Something you've been doing for fun on Saturday mornings might be part of it. A skill you've developed over 15 years in corporate America might eventually become useful somewhere you can't see yet.

You don't have to know. You have to be willing to try.

 

Where This Leaves You

People all over the world are changing the way they experience life, and many of them are starting from circumstances just like yours.

They have jobs, families,, financial responsibilities, careers they've invested years into. They aren't all millionaires, entrepreneurs or all quitting their jobs. Most didn't have some perfectly constructed master plan before they began. They started where they were.

That's what I want you to hear in Grayson and Marie's story.

The distance between the life you're living and something different doesn't always begin with a giant leap. Sometimes it begins with changing the question you're asking.

Instead of saying to yourself If only...

Change that question to What if...?

Then go find out.

Maurice, Try Life On