What’s a lesson you didn’t expect to learn but now never forget?

[BrianaJo]

You know those oddly specific lessons you only learn after you’ve been running your business for a while?

Like realizing your milk delivery driver blocks the morning rush if they park in the wrong spot.
Or that letting someone “help out” with free content might haunt your branding for six months.
Or figuring out your pastry case looks best at exactly 2:17pm and not a minute sooner.

I’ve been reflecting on how much of this business isn’t stuff you can Google. It’s just stuff you figure out, fix, and then remember forever.

What’s one of those moments for you? Something random you had to learn the hard way, but now it’s a core part of how you operate? 

I’ll start. Gregory and I built all our bar processes around his height. He’s 6 feet tall, and at the time it made perfect sense. He was the one working behind the bar every day, so we designed everything to feel smooth and efficient for him.

It worked great… until we started hiring. Turns out most people aren’t 6 feet tall. Our current baristas are closer to 5'5", and while they manage just fine, there are still a few tasks that require some creative stretching, tippy toes, or a trusty stool.

Lesson learned. We're redesigning the next space with more height flexibility in mind.

[BofBArtStudio]

If you think you're going to want to replace the flooring in your space, don't assume that you can do it later.  Replacing the flooring down the road, after you've been running for several years, is just very difficult because of all of the things that you have in your space. Equipment, check out desks, shelving full of merchandise. 

When we first started, and the building was empty, We thought the floor was okay. It was an ugly tile, but we knew the price tag that would be involved for a 4,000 square foot place to remove all the tile and install new flooring. 

So we decided to leave the ugly tile for later.

Now 11 years later, we have said many times how much we would love to replace the flooring, but it just seems impossible. It would require probably closing down for a month, renting some kind of large storage, and emptying out pretty much everything. 

Even if we did it in sections, which would be more costly and less efficient, we would still need to be moving everything around to clear a section at a time and shove everything into the sections that weren't being done at any given time. 

It just seems like a daunting task and so we continue to live with the ugly flooring that we have.

[indianathomas]

The biggest lesson I’ve learned in business? People are going to do what people are going to do.

This ties directly into the Stockdale Paradox—the idea of confronting the brutal facts of your reality while maintaining unwavering faith in your long-term success.

In the early days of building Keva, I took everything personally—when someone quit without notice, called out with outrageous excuses, or ghosted a shift at the worst possible time. I’ve heard every version of “emergency” imaginable: unexpected vacations, the passing of distant relatives they hadn’t seen in decades, and even “I’m **bleep**ting blood” texts.

Meanwhile, I missed countless T-ball games and family moments because someone didn’t show up, and the store had to stay open. Back then, cash flow was tight. You couldn’t just throw $50,000 a year at someone to make smoothies or lemonade. We worked hard to create a fun environment—offered good pay, free product, and treated people respectfully. Still, disappointment was part of the package.

Eventually, I realized: it’s just people. They’ll come and go. Some will lie. Some will steal. Some will make your day, and others will ruin it. But the key is to stop taking it personally.

That’s the Stockdale Paradox in action—acknowledging the messy, unpredictable, and often painful realities of running a business, while continuing to believe in the bigger mission and the long game.

I don’t get upset anymore. I take the high ground, keep building, and focus on what I can control. That mindset has brought me more peace—and longevity—than anything else.

[RuckusDonuts]

Easy....

That starting your own business from scratch, including the buildout, is in many ways like having another child. You simply can't decide "I don't want to parent today". Ditto with being an entrepreneurial owner. 

[KateV]

Wow! What a great topic! In my 7 years of running this business, I've learned a lot, especially about people management. It's been the hardest aspect of business for me and my biggest learing curve. Here are my big three lessons - some are difficult, so feel free to skip ahead if this isn't the right time for you. 

The business owner is never part of the group

As an owner, it's hard to find true fellowship with your team. It's vital to connect with other entrepreneurs who understand the unique challenges we face. 

Learn how to hire slowly and fire fast

1. It's important to take time to hire the right people, but once you know it's the right fit, act quickly. Here's a method for delivering difficult news, if needed: 
2. If possible, hold an in-person meeting and start with: "do you know why I wanted to meet?" 
3. If they say yes, you can proceed quickly. If they say no, follow up with: "Today is your last day with our company." 
4. Let them know this decision is final and not open for discussion. 
5. Offer a follow-up meeting in two weeks to discuss further, if necessary. 
6. Make sure they return all company property and inform them when to expect their final paycheck
7. If health insurance is involved, explain where they find their COBRA benefits
8. Document Everything

Difficult situations with employees

I recently hired someone who was with me for 6 months and has recently been let go and has since caused some challenges in the business. This person was in a leadership position, and while I could not have detected it at the time, I've since learned they may have a personality disorder. It's important to understand how to navigate such situations to protect yourself and your business. Here are some insights from experts Dr. Martha Stout and Dr. Patric Gagne: 

• Sociopathy affects about 1 in 25 people. While they don't necessarily break the law, they may challenge boundaries and lack empathy, (and fear) 
• People with this disorder often mask it well, adaptiing to social cues and behaviors to blend in. 
• The are often in a chronic state of apathy, and are competitive to the point of winning at all cost. This may manifest in overstepping responsibilities, failing to admit to wrongdoings, chronic and easily disproven lies. 
• The best way to manage these indivisuals is to avoid engaging emotionally with them. They thrive on manipulating reactions, so if we don't react, their game loses its appeal. (the only real tell reported is "the pity play" They want to be pitied because being in a state of pity for someone is when we let our guard down and make excuses for people and can be easily manipulated)
• Always document your interactions to safeguard yourself and the business. 

[Maurice8th]

My focus on revising my business plan when I didn't know what my business plan was going to be? Yeah...that happens!