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9 Ways to Be the World’s Best Boss to Yourself as an Entrepreneur



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Do you remember that scene in the very first episode of The Office where Michael Scott talks about why he’s such an amazing boss and then shows his World’s Best Boss mug… that he bought for himself? Confession: I am an entrepreneur (technically a solopreneur) and I bought myself a World’s Best Boss mug! It’s my reminder that since I’m the boss, I need to be a good boss to myself.

To figure out how to be a good boss to yourself, think about a good boss that you’ve had. Why were they a good boss? Or think about a terrible boss that you had. What do you wish they had done differently? After five years as an entrepreneur, first as a successful blogger and now as a productivity coach for entrepreneurs, here’s my list of how I can be the world’s best boss to myself: 

1. Invest in Training and Education

A good boss cares about your long term career growth. They might send you to conferences, pay for continuing education, or provide one on one coaching to help you prepare for a promotion. 

When you’re the one footing the bill and carving out time for these kinds of things, it can be easy to put them off. However, you hurt your personal and business growth long-term when you avoid investing in training and education for yourself. 

2. Prioritize Mental and Physical Health

Any kind of job can take a large physical and mental toll on your health. A good boss cares about the health of their employees. There are ways to care for your mental and physical health as an entrepreneur that can fit any budget or amount of time you have. 

  • Take 15 minute breaks. 
  • Get a gym membership. 
  • Stay up to date with doctor and dentist appointments. 
  • Set a water drinking challenge for yourself. 
  • Schedule mental health days off. 

The options are endless. Be a good boss and take care of your health. 

3. Recognize Accomplishments

It sucks to do a lot of hard work and have no one recognize or appreciate it. When you work for yourself, you take on the role of the hard worker and the “appreciator”. 

End each week by writing down a few of your wins. When you reach your goals, celebrate the achievement by going out to a fancy restaurant or doing something special. 

4. Make Work Fun

  • Play music when possible
  • Taco Tuesday
  • Holiday decorations in your office 
  • Pajama day (or a dressy day if you’re usually in your PJs)
  • Lunch with friends in your field to share ideas

Anything you do to mix things up and add some festive spirit will make your workday feel fun and fresh. 

5. Set Clear Goals

It’s frustrating to work hard and feel like you’re not getting anywhere — or to have no clue what you’re working toward. A good boss makes sure that the whole team knows what the goal is and tracks the progress. 

You can easily do this by setting clear goals — which means that you will clearly know when you’ve achieved your goal. Sign 5 new clients = clear. Get more clients = unclear. Bonus points if you create a chart to visually track your progress. 

6. Motivate

A good boss can motivate their employees, even when the task at hand is less than fun. Motivation is an emotion that is created by your thoughts, which means you can gain motivation by choosing your thoughts intentionally. 

A great way to do this is to think about why you want to do each task on your schedule. How will the task help you get closer to your goal? How will finishing the task benefit you? When you know why something is important, you’ll be more motivated to do it. 

7. Be Decisive 

It’s easy to constantly flip-flop and try new methods when you’re a small business. But unless you stick with each method long enough to fully understand it and see if it works, you’re just spinning your wheels. 

You may go all in on building your email list until you hear about amazing results someone else is getting on Instagram. So you dive into Instagram until you hear about another person’s success on LinkedIn. 

A good boss is decisive. They decide what needs to be done and how it’s going to be done and then sticks with it until it’s time to reevaluate.

Be decisive. Choose your method and stick with it until you have enough data to evaluate and make your next decision. 

8. Welcome to New Ideas and Creativity

As a boss, if you aren’t open to new ideas, your employees will get the hint and stop suggesting them. All creativity will end. You can be open to new ideas as an entrepreneur by setting aside time to brainstorm with no filter. Allow your ideas to be completely out-of-the-box. A lot of them won’t be worth pursuing, but your golden idea will only emerge when you are willing to get creative. 

9. Give Time “Off the Clock”

Have you ever had a boss that calls or texts you when you’re not working? It’s hard to relax when you can’t leave work at work and get some proper downtime. Don’t be that guy. 

Give yourself time off the clock. Close your office door after work or turn off your phone if you need to. If you’re a solopreneur, you may feel the need to always be reachable. But never having time away from work is a great way to get burnt out. Be a good boss and “clock out” for a bit.

When you’re an entrepreneur it’s easy to unintentionally be a crappy boss to yourself. But with a little intention, and maybe a new World’s Best Boss mug, you can be a great boss and propel your business to higher success.

Christine White is a work-life balance coach for entrepreneurs and the creator of the Check-Boxes Planning System. She helps online entrepreneurs grow freedom-giving businesses while enjoying their beautiful lives. You can join her monthly coaching membership via her website.

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