As an entrepreneur, one of the most exciting moments is when you start hiring team members. You accrue new employees who believe in you enough to want to join your company. However, on the flip side of that excitement, hiring employees brings with it a lot more responsibility. Because of how tumultuous a business can be when it’s first starting out, you will often be faced with a lot of difficult decisions that affect the lives of other people, including firing people. Hiring and firing deeply changed me as an entrepreneur, which is why I wanted to share with you how these events will change you. 


While every time you hire someone is exciting, nothing will beat your first time. Because that means you finally have been successful enough as a business that you have the money to pay a person’s salary. You’re no longer on this journey alone – you’ll have someone to lean on and navigate growing your business with.

Hiring your first employee will take longer than you think. You’ll feel impatient and want to hire someone sooner rather than later, but at the same time, you’ll want the perfect candidate. You’ll talk to more people than you will for any other position you’ll ever hire for, but when you find the person, you’ll know it’s the right one. Then, the feelings of excitement will come rushing back because you’re about to become more than a solopreneur. It’s the beginning of feeling like a real business.

You’ll always feel differently about that first employee because they believed in you first. They took a leap of faith to join you, and in return, you’ll feel closer to them than any other employee you’ll hire as an entrepreneur. You’ll give them more opportunities to provide input on the direction of the company and seek their advice whenever you’re facing an obstacle you can’t overcome alone. And that’s OK. Your employee will appreciate your confidence and take advantage of the opportunities you provide. 

After the first hire, the sheen will wear off a little. You’ll still want the right candidate, but you already have a right hand (wo)man. The hiring process will never get easier, but you’ll feel less pressure when making the decision. 


Of course, firing is a shitty time. I don’t need to tell you that. 

There will be a moment when you know an employee isn’t working out, and they can’t be saved. Maybe they’ve been reprimanded before or they haven’t been doing well in their reviews, and you don’t see a course correction in their future. That moment, when it comes, will alter your every day until the situation is rectified. Because if you’re thinking you’re going to only have to fire someone because they were an asshole or slacking off, you’re wrong. You’ll have to fire people because they fall behind, they don’t work quickly, they mess up one too many times with a client, or you don’t have enough money to pay them. Regardless of the reason, you will feel like YOU failed them.

Part of the reason you won’t want to fire them is because you’ll have to swallow your pride and admit you failed. Even though you may feel like that’s selfish, it’s not. Because your failure will result in someone losing their source of income and experiencing unexpected financial strain. Regardless of what THEY did, you will feel the guilt and failure. And those feelings won’t go away after you’ve fired the person. Those feelings will hang over you for a week, and you’ll feel them every time you need to let someone go. That’s why it’s better to get it done when you know it’s time rather than dragging it out and hoping the situation corrects itself. 

And if you’re wondering how to fire an employee, there is no right way. There are a lot of wrong ways, like getting emotional, being unable to provide concrete reasoning for your decision, or doing it via the phone.  But there is no right way. Just be sincere, understand the person’s feelings, and give them time to process. 

If you’re looking for more resources on building your team and internal culture, check out our team and culture education page

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