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15 of the Most Difficult Things When It Comes to Transitioning from Employee to Employer

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

Career transition from employee to employer

The following answers are provided by members of Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

1. 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.

Vik Patel, Future Hosting

2. 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.

Jeff Cayley, Worldwide Cyclery

3. 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.

Kim Kaupe, ZinePak

4. Letting Go

As an employee, I had an attitude of taking on everything I could, and it brought me great success. But as an employer, taking on everything just simply isn’t possible. I had to learn what to let go of, to save both my sanity and the quality of my work. To succeed in entrepreneurship, you have to learn where to focus your strengths, and what to delegate to other experts.

Elle Kaplan, LexION Capital

5. Drawing a Line in Friendships

Shifting from an employee to an employer within the same company required that I evaluate the depth of my friendships at work. Knowing the intricate details of employee’s lives can make some decisions more difficult when it comes to lay-offs, compensation or performance issues. I love my work family, but I have to remember that there is more at stake than personal relationships.

Angela Harless, AcrobatAnt

6. Being an Outsider Amongst Employees

You’ll need to come to terms with the fact that you’ll always be an outsider to your employees, not someone like them. No matter how hard you try to relate as just another employee, you’ll always be seen differently and not be able to experience firsthand discussions that employees have amongst themselves.

Mark Cenicola,

7. 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.

Michael Spinosa, Unleashed Technologies

8. 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.

Brandon Stapper, 858 Graphics

Entrepreneur at a startup center

9. Being Clear About Who Makes the Decision

Decision-making ability is something that flows from the top, and sometimes people are scared to say, “I have final say on this one,” so they resort to group-based decision-making. That almost never works, and it often leads to confusion around roles and responsibilities. As an employer, make it clear what decisions you make and what decisions you’re delegating to others.

Mattan Griffel, One Month

10. 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.

Tolga Tanriseven, GirlsAskGuys

11. 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.

Shawn Porat, Fortune Cookie Advertising

12. Passing the Torch

The hardest thing about transitioning from an employee to an employer would have to be allowing someone else to handle your job. We all have faced that stigma which is “no one works harder or better than yourself.” I personally aim for my employees to at least meet or exceed my abilities; it makes me feel more secure when I leave town knowing that everything is taken care of.

Luke Sanchez, HMG

13. Letting Someone Go

There are times when I have to let someone go, and it is often exceptionally difficult because my employees feel like family to me — especially if they have been with the company for several years. I also have difficulty in knowing that they have dependents, and I worry about their ability to find suitable employment after they leave.

Luigi Wewege, Vivier Group

14. 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.

Brittany Hodak, ZinePak

15. 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.

Alexandra Levit, Inspiration at Work

About author

The YEC 91 posts

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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