5 Lessons from 5 Years in Business

“There is joy in the grind we choose.”

Those eight words have been etched in my mind since a fellow business owner said them last year.

We were talking about the highs and lows of owning and running a small business — the sleepless nights, the mental exhaustion, the sacrifices no one else really understands. That’s the grind.

But in the same breath, we delighted in the indescribable satisfaction that comes from getting to choose that grind. To build something from nothing. To make an impact, change lives and be free to do what you believe is right every day. That’s the joy.

As Round Square celebrates its fifth birthday this month, today is an ode to the grind and the joy and what we can learn from living between the two.

The Grind & the Joy

Nearly half of the more than 32.5 million small businesses in the United States don’t survive past five years (Small Business Administration).

HALF. Let that sink in for a moment.

As Round Square blows out five candles on our virtual birthday cake and raises a glass to breaking through that ugly statistic, the truth is that both halves deserve celebrating.

Entrepreneurship is never linear. Heck, owning a business wasn’t even on my radar or in my life plans. Ever. Like many business owners, Round Square was born from witnessing too much complacency and mediocrity in the nonprofit sector and believing something better was not only possible but required.

During our first five years …

• We’ve received our certifications as a Woman-Owned Small Business and Women’s Business Enterprise by the Women’s Business Enterprise National Council and the State of Florida.

• We’ve made the 2023 top 100 list for fastest-growing businesses owned by a Florida State University graduate.

• We’ve significantly increased audience engagement and fundraising for numerous nonprofits and transformed the mindsets of countless nonprofit leaders.

And that’s just the beginning.

The Lessons

What has the grind and joy of owning a small business for five years taught me? As it turns out, A LOT. Here are five takeaways that can help anyone become a better leader, business owner and human.

1. Excellence is everything.

The most successful people and businesses — the ones who will really change the game — are allergic to mediocrity. They are relentlessly curious. They ask questions. They don’t settle for enough or good enough — instead, they say “enough is enough” to cookie-cutter approaches and tired strategies. They bring their very best each day they are given because they believe more is possible — they believe better is possible. Perfection is not the goal; your very best is the goal (and sometimes, that looks different on different days). The most meaningful way to attract and grow your business is through your performance. Keep doing great work, and more work will come.

2. Growth often comes from discomfort.

It’s hard to remember in the moment, but struggle, failure and even fear are good for us; in those moments of discomfort, we grow and become stronger. During the past five years, there have been many instances where I’ve briefly asked myself if I’m in over my head on a particular project or if I can unravel the solution to a tough challenge. But, as the saying goes, if you’re not a little afraid, you’re probably not doing it right. The only way is through, and on the other side something amazing is waiting for you.

3. Don’t be afraid to focus.

When I first started Round Square, I was nervous about focusing only on nonprofit organizations. Would that prevent me from getting business? Would I be closing the door to opportunities? The opposite was true. Being laser focused and an expert in your field often makes you and your business more desirable. It’s the same reason you want to take your child to a pediatrician rather than a general practitioner. No one is an expert in everything. Be an expert in what you do best, then be the very best at it.

4. Be generous with your time.

I once had a business owner charge me $250 to have an initial call with her when she knew I was serious and interested in finding a partner. Spoiler alert: the relationship didn’t work out. That’s because true partnerships and trust are built on relationships. People who genuinely want to help and support others know that when they do the right thing, the right things happen. Be generous with your time and counsel. Yes, there are never enough hours in the day, but take the call, have the lunch, share your perspective during a Zoom chat. It’s how you build your network, relationships and trust. Potential clients and those in your network will remember the person who took that extra time with them, shared their honest and authentic perspective and put the best interest of others before their own.

And don’t forget to participate in the life of your clients’ missions. At Round Square, our mission is to help our clients achieve theirs. Participate in their events, donate time throughout the year or sponsor one of their initiatives. Be generous with your time, your talent and your treasure. Generosity breeds generosity.

5. Care the most.

Last but not least, be the champion of caring. Care about your work and the people you do it with more than anyone. Care about the issues. Care about the details. Care about people and relationships and what others say (and don’t say) that they need to be successful. Say thank you a lot, then say it again, then show that gratitude through your actions. Pay people what they’re worth, which is often more than what they think they are worth. Win in caring, and you will win at everything.

To everyone who has supported Round Square, worked with us, shared their friendship and been an ally for change, we say thank you. Cheers to being in the one-third of small businesses that make it to 10 years.