5 Powerful Catchphrases For Entrepreneurs To Live By

Photo by Ryan Higgs, 5 Powerful Catchphrases For Entrepreneurs To Live By

When John Spain says, “I’m coming off the busiest two months of my life,” he means it.

His fine arts gallery across the bridge from Dock Square in Kennebunkport, Maine, just went through a massive expansion. This past winter, they constructed seven brand-new “micro-galleries” that include studio space for artists, printing, and framing. They acquired another gallery across the road from their newly renovated main building. The whole operation, dubbed Maine Art Hill, now includes nine distinct, walkable buildings. I’m not even going to get into the Kennebunkport Festival. So, yeah. A lot.

I’ve known John for over a decade. He took a chance on me as a college freshman with virtually no experience in fine arts or customer service and did his best to mentor me in the business. I spent five summers working at the gallery and still count it as one of the best jobs I ever had.

I wanted to interview John because I think he’s a paradigm for a successful entrepreneur. No, he didn’t start Facebook. But most of us aren’t trying to start Facebook. We’re trying to start a very profitable business and be part of a community.

More importantly, John is a self-made man. He never went to college and had little to no financial support when he struck out on his own after high school. So many of the stories we hear about successful entrepreneurs include some kind of sneaky footnote about their family money (don’t take my word for it), but John is living proof that you can make it if you work hard, play smart, and live by your principles.

By principles, I mean mottos. Maxims. Proverbs. John is a guy who loves his catchphrases and really sticks to them.

So how do you make it as the little-guy entrepreneur in a global economy of very big fish?

Here are John’s five best catchphrases for entrepreneurs to live by:

“Will you regret it more if you do it and fail, or if you don’t ever try?”

This is the ultimate question that new and would-be entrepreneurs should ask themselves.

This is the question that John asked himself, and at twenty-three years old he decided to pour all of his time and energy into building a business. He bought a small print and framing shop for next to nothing and worked at it harder and smarter until it became profitable.

When you ask yourself this question, do it thoughtfully. Consider each side of the equation and your honest emotional response. Not every entrepreneur has nothing to lose. Many have families and other obligations. Would the risk of failure be catastrophic to you or your family? Would you be able to pull yourself back up again?

This question isn’t just meant to inspire you to follow your dreams of being an entrepreneur. It’s meant to help you assess if this is really the right path for you.

“Ninety-five percent is enough.”

“That last five percent is just for you,” John likes to say. “At ninety-five percent, you’re golden.”

If you’re insisting that every project or product is 100% perfect, then you’re too afraid of failure to be innovating and expanding. You’re not trying hard enough. You’re not failing enough.

The fact is, nearly every client is going to be pleased with ninety-five percent of perfection.

There’s a bigger lesson here about letting go of control. According to John, the most pivotal adjustment he made as a businessman was recognizing that he did not have to do “every little thing,” that his way was not the only way.

By giving a little leeway and authority to his employees, John created room for the innovation that allowed his company to grow. For example, he lets his manager sift through applicants, so he only spends his time interviewing the people he hires.

“It’s better to ask forgiveness than permission.”

This is my all-time favorite of John’s catchphrases. Its applications are endless.

In the summer of 2007, Maine Art Gallery was installing a new kinetic sculpture on its grounds—a big one. The tip of this sculpture was going to be 32 feet above ground-level, just one foot under code.

It was also copper and constantly moving. Did the standard building codes apply to giant, spinning, metal lightning rods? John decided it would be better not to ask until the base of the sculpture was solidly fixed in a few thousand pounds of concrete.

So what did the town think? Everyone loved it. No problem with the building codes, and every day people gawk at the enormous (yet graceful!) Wind Sculpture.

Entrepreneurship is all about taking strategic risks. As long as your intentions are good, you can often spare yourself a lot of hassle by simply doing the thing. Just remember that this isn’t an invitation to be reckless. Don’t gamble away your life’s savings and expect forgiveness. Always have a backup plan. We could have pulled the Wind Sculpture out of the ground without too much difficulty if we had to.

“A rising tide lifts all ships.”

When John turned Maine Art Gallery into Maine Art Hilladding seven new gallery spaces and taking over Gallery At The Grand next doorhis goal wasn’t to crush his competition. It was to help it. Those new spaces are meant to be rented by fellow Maine galleries and artists not formally affiliated with Maine Art.

There’s a strategic advantage to inviting like-businesses to cluster together, creating a destination experience. But there’s a bigger reason to cooperate with your competition. Collaboration leads to new opportunities. And stronger communities mean stronger economies.

This doesn’t mean you should be casually referring customers from your hardware store to the hardware store down the road.

What it does mean is that you should always be looking for ways to work with the businesses in your neighborhood (or your community) and finding ways that your services compliment each other.

“Life will lead you around by the nose if you let it.”

In this case, “being led around by the nose” is a good thing. Think about a bunch of pleasant smells.

The point is this: if you need something, put out that request into the universe with some positive energy and optimism. Your needs will often be answered, though maybe not in the way you expect. The flipside of this maxim is also relevant.

“If I have to beat my head against a wall to get something done, it probably means I shouldn’t be doing it,” John explained, who measures the value of an idea in terms of headaches.

Take, for example, an unrelated business John was trying to buy for the past three years. Three times, he believed he had the deal finalized. Each time, it fell apart. Finally, John said, “I’m done.” And just a few months later, the opportunity to build the micro-galleries and create Maine Art Hill presented itself.


Catchphrases, mottos, proverbs… Call them what you will, they’ve never meant that much to me.

That was until I started to really think about it. “It’s better to ask forgiveness than permission” has stuck with me for years. I fall back on it frequently (perhaps more than I should).

“Will I regret it more if I don’t ever try?” is another question I ask myself frequently, in all kinds of circumstances. I actually hear those very words echoing in my head.

Words have power when they hold truth. John’s trusty sayings might be just a few words long, but they have proven value for entrepreneurs. What words have been useful in your career? Be on the lookout for your own guiding phrases. You never know whenor whothey might help.


Ryan Cadigan
I write about people making changes in their lives and the world--health, spirituality, politics and the environment. Background in startup marketing, MFA in Creative Writing. The skinny at rccadigan.com


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