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Question: What one thing did you find most difficult when transitioning from employee to employer?

Setting Work/Life Boundaries

“When you’re an employee, someone sets boundaries for you. When you’re an employer, it’s all to easy to become obsessively focused on the job. For me, the most difficult thing was to realize that, because I hire the right people, I don’t need to work constantly and supervise everything. The result: I’m happier, more focused, and more likely to develop the ideas that will move my company forward.”

Checking in With Employees Regularly

“As an employer, you have to constantly be checking in with people and making sure they are happy with their role and everything else. This is time-consuming and very hard to delegate. As an employee, it isn’t your responsibility to check in with other employees. “

Taking on the Problems

“The most difficult transition from employee to employer was the lost use of the Forward button. As an employee, when I faced a problem I couldn’t solve or handle I would forward that problem to someone else — accounting, legal or my boss. As the employer, the email stops with you. If anything, you are now the receiver of said problem.”

Finding Confidence in Your Position

“When you make that big transition, it’s easy to second-guess your approach when challenged by a member of your team. You must have the wisdom and experience to understand when that person is correct or when your path is best, insisting that a team member stay the course despite his/her protest. This is a very difficult task and it is a skill set that you will always be developing.”

Needing to Work Harder Than Ever

“An entrepreneur is a “sexy” thing. I thought I would start my company and make millions in the first year. The most difficult thing is realizing that you need to work 100-hour weeks for years to keep your head above water. I wasn’t aware of the amount of persistence and dedication required to start and run a small business. Your brain never shuts off and you are always working.”

Caring Too Much

“As a good employee, you care a lot, and even get frustrated due to failures or due to other people. But afterwards, you can move on even if the problem you were frustrated about isn’t fully handled or won’t ever be. And you are OK with that. But as an employer, you can’t not care even if you try. Sometimes that can lead to caring too much, which causes burnout and excessive stress.”

Seeing the Big Picture

“When you’re an employee, you can be hyper-focused on your own particular specialty. When you run a business, on the other hand, you always have to be looking at the big picture. As an owner, everything that happens in my business has to be a concern to me. For the most part, I’m comfortable with this, but as a business owner, it’s something you have to keep in mind at all times.”

Understanding What Motivates Employees

“I have to remind myself that not everyone is entrepreneurially minded, and everyone is motivated by different things. Something that is completely meaningless to one person (like a title change) might be very important to another. Taking time to learn those nuances, and making time for “softer” issues — like helping employees with intrapersonal communication challenges — is critical for team success.”

Feeling Insecure With the Unknown

“I’ve now been an entrepreneur for 12 years, but I am still uncomfortable with the uncertainty that comes with the territory. When I was an employee, I knew that if I did what was expected, the paycheck would come reliably every two weeks. In my own business, I’m never sure what my profit will be year to year, and I worry about effectively supporting my employees, vendors and family.”