Become the Best Boss You’ve Ever Had

Advice for fellow entrepreneurs from a former tyrant.

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The best boss I ever had was named Dawn. She set clear expectations, coached me through difficulties, and showed her appreciation at every opportunity. If I put extra time in on a project, she’d give me an unexpected day off. She helped me prioritize my time and challenged me to do things I didn’t think I could do. Dawn expected the best from her team but accepted failure as part of the learning process. She did everything she could to make work fun!

I left Dawn to work for a tyrant. My new boss worked me seven days a week without breaks. Forget fun! Everything was a priority, and I had to get it all done…or else. When I failed, she verbally berated me, and rarely took time to celebrate my successes. She put everyone’s needs before her own, and as a result of working for her, my physical and mental health began to fail, and relationships began to suffer. That boss’s name was Donna. To be clear, that boss was me.

For the last twenty years, I’ve been working for myself, and I have loved most of it. The people, the work, the experiences have been incredible. However, because of my boss, I almost lost it all. Fortunately, she’s beginning to smarten up.

Most of us enter the entrepreneurial life with thoughts of freedom, adventure, and the profound difference we hope to make. Before you know it, however, we become the very bosses we dreaded working for in the corporate world. What if we stop that right now and strive to become the best boss we’ve ever had? Here are a few of the ways I’m trying to do just that. Perhaps they will help you as well.

Set and Keep Boundaries. You can still give exceptional service and have boundaries with your customers. For instance, I realized that if I take meetings with customers and others at all hours of the day, there’s no time left to work on their projects. So, I use the calendly app to offer suggested times for video chats and rarely deviate from my pre-set availability. Likewise, you can set boundaries around how much you’ll travel, which days you’ll work, when you’ll respond to email, and when you’ll stop working for the day. The key is to be clear about the way you work so your customers know what to expect. Do I make exceptions? Yes. Occasionally. However, I’m learning that I’m not at my best without boundaries, and that doesn’t serve anyone.

Prioritize Your Health. There was a time, not so long ago, when I got through a long day at work by eating bags of chips to help keep me energized and awake. Fitness was squeezed in or forgotten. Cups of coffee and Coke Zero were the “fuel” that kept me going. Unfortunately, those behaviors took their toll. Today, I think of keeping myself healthy as a vital part of my job. I’ve invested in a nutritionist, take live-virtual fitness and dance classes, hike at least five days a week, and have found doctors who focus on preventative medicine. Water is my drink of choice, and I strive to get plenty of sleep. As you might imagine, this has resulted in more energy and a clearer mind and only increased my focus during work hours.

Learn to Say No. With all due respect to Shonda Rhimes and her Year of Yes, most entrepreneurs would benefit from a year of no. If you cram your calendar with every networking opportunity, every workshop, “customers” who can’t pay you, and a slew of volunteer roles, there’s no room for inspiration and creativity. You don’t want to be one of those bosses who overwork their team! Help yourself prioritize the few commitments that make the most significant impact and let go of the rest. You’ll be happier, and you’ll reach your goals sooner.

Take Time Off. Negotiate more vacation time with yourself. It took twenty years in business to realize that I don’t want a company that ran my life, but rather one that supports my desired life. Weekends are for downtime, and vacations go on the calendar before anything else. I no longer buy into the theory that “if you love it, it’s not work.” Sometimes, it’s still work, and it takes time away to feel rejuvenated. As a bonus, you’ll meet people and have experiences that will kickstart your creativity when you get back to it.

Have Self-Compassion. You’ll make mistakes; plenty of them. But, frankly, it’s the only way to grow both personally and professionally. A tyrant boss will beat you up for them. A compassionate boss will stay with you as you feel inadequacy, embarrassment, and fear. She’ll help you move past them and find the lessons. She’ll cheer you on as you come back stronger than ever.

Build a Solid Foundation. “You’ve got to spend money, to make money.” True, to a certain extent. However, not to the degree that all the people trying to sell us stuff would have us believe. The amount of stress I caused myself by signing up for coaching programs I couldn’t afford, purchasing the latest and greatest software before I was ready, and growing my team way too fast was overwhelming. Today my boss (still me) knows that one of her jobs is to build a solid foundation for the company first to minimize the anxiety that can only negatively impact the organization, customers, and the team. This means pausing before jumping into any new opportunity and asking three questions. Is it good for the team? (even a team of one) Does it benefit our customers? Is it fiscally responsible? If she can’t answer yes to all three of those, it may be a no…for now. It means putting money away from every single deposit to build business runway (backup funds) and never letting the account drop below a certain number. (hint: the number isn’t zero) Good bosses create the conditions for financial peace of mind, which gives their team members the freedom to create, serve, and work with purpose.  

Celebrate Your Successes. Do you want a boss who constantly pushes you to do more, achieve, and keep going? Or do you want a boss who appreciates the work you put in and celebrates your success? Be the second boss. We sometimes get so caught up in how far we have to go that we forget to reflect on how far we’ve come.  

The irony is that my business is picking up like never before as I commit to these “best boss” practices. Despite (or perhaps because of) the commitments I’ve made to myself, everything I had hoped to achieve is happening naturally. More importantly, I’m so much happier! When you take care of yourself first, you’re better able to help others, and your success (however you define it) will follow.    

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