Permission To Love Your Small Business

Bryan Hendley
5 min readJan 30, 2025

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Photo by krakenimages on Unsplash

This theme has come up several times in conversations with both friends and clients over the last few weeks.

When I use the term “Small Business” I’m thinking about a business owner who is directly involved in operations, even if it’s primarily from a leadership position, with a team of 1–5. That’s just my perspective for the sake of my work, my clients, and my sharing. I understand that there are other definitions for other people, but I want to be clear on where I’m coming from.

Also, some of my clients have a team of 3 that serve as their leadership team, and then 10–20 technicians, laborers, or other individual contributors. So, there is certainly some flexibility here.

Anyhow, as I speak to friends and clients who are small business owners, several of them are dealing with challenging employees to the point that they are no longer enjoying their business.

For some of them, it’s easy to put their finger on the problem. The employee is disrespectful, difficult to deal with, or doesn’t fit well with the team.

For others, they can’t quite put their finger on the issue, but the employee just isn’t a good fit and is causing undue stress on the owner and their experience in their business.

Sometimes, the people I speak with don’t feel as if they can move on from the challenging employee due to their expertise within the company or their performance. In other words, while they are a pain and often cause other issues, their output is a positive for the company and the owner feels as if they would be hard pressed to replace them.

Other times, the owner simply feels bad. This is where and why my definition of small business matters. Poo poo it if you’d like, but when you are a “small business” owner, it probably means you built this thing on your own and then added others to the mix. You are probably learning on the fly what it means to lead others, deal with a team, and all of the challenges that come along with that.

Perhaps, as one of my friends is experiencing, you took on your very first employee, someone that you may have already had a relationship with, and now you are learning that it’s not a good fit.

So, you feel bad. Maybe it’s your fault as a leader that you can’t get them aligned to your values. Maybe it’s your fault that you weren’t more thorough in the interviewing and hiring process. Maybe it’s your fault for hiring someone in the first place. Maybe you weren’t ready. Should someone else suffer because of your mistakes?

These are the questions you may ask yourself as you wrestle with what to do with your employee. And what I’m seeing is that many small business leaders choose to hold on and often for the wrong reasons. They don’t want to hold the challenging employee accountable. They feel guilty for not being able to hold them accountable or for hiring them in the first place. Or they are simply scared to let them go.

So they let them stay. And it has a negative impact on their team, their business, and on the business owner. They end up hating going to work.

As I shared with one of my clients, if you want to hate your work, just get a 9–5, go home when it’s time to go home, complain about your boss, and leave your work at work. It will be way less stressful.

Of course, I’m sort of joking. I realize everyone doesn’t hate their work and complain about their boss when they work a 9–5. And I certainly don’t believe a 9–5 is bad, or less than. However, most business owners got started because they wanted to create their own thing. They wanted to be their own boss. And they probably started out doing something they enjoyed.

Work can be hard and we won’t always enjoy everything, but generally speaking, we should at least allow ourselves the belief that we can enjoy our business, and maybe even love it, as small business owners.

A couple of caveats:

  1. Absolutely, we should do our due diligence before hiring, especially when we are hiring for the first time. If we owe anything to the people we are hiring, it is that we should not do so recklessly, or be inconsiderate of the fact that someone is trusting us for a job.
  2. We should do the necessary work to coach, train, and lead our people. Preferably, we don’t want to be firing people simply because we are afraid to have the tough conversations or unwilling to do the work that is necessary to lead through challenging times.

That being acknowledged, what I keep coming back to is this:

  1. If you “deserve” anything as a small business owner, I think it’s the ability to enjoy going to work. It’s your business. You shouldn’t have to hate it because of someone else.
  2. The people you hire should value what you value. If not, they probably aren’t a good fit in your small business. If they don’t value what you value, or can’t get behind valuing what you value, how will your small team succeed considering the amount of intimacy, trust, and teamwork required in a small business?

That might mean owning your mistake and sharing with your employee that your business can’t handle the additional payroll at this time, and finding a way to move on that works for both of you.

Maybe it means a tough conversation about their inability to buy in and commit to your way of doing things.

Maybe it means an honest admission that it’s simply not a good fit, and as a small business owner, you aren’t able to spend any more time or money trying to make it work.

Be considerate, be measured, and be diligent in knowing you’ve done everything you can. And, give yourself permission to love your small business.

I’m pulling for you,

Bryan

I write encouragement on leadership, business, and personal development.

I help small business leaders lead, grow, and build in a way that is aligned with their values and sustainable.

You can learn more about me and check out my business coaching services at www.efournine.com.

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Bryan Hendley
Bryan Hendley

Written by Bryan Hendley

Writer, Strategic Coach for Small Business Leaders - I write encouragement focused on small business, leadership, and personal development. www.efournine.com

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