When we jumped into this latest mini-retirement, I bought myself a new mug. Partly because I’m obsessed with mugs. But I also knew I would need a reminder. Something to keep me on track and focused. My goal was simple: Become my own Best Boss Ever.

Over the last 20 years, I’ve worked at lot of jobs. I’ve had a LOT of bosses. Some companies and bosses were incredible, inspiring and made work awesome. And from good bosses to less-than-steller ones, I learned what made a great boss for me. My goal was to be that to myself.

This is surprisingly challenging.

We all want a great boss. But I find very few people are willing to give to themselves what they would want to recicieve from a boss.

We want someone else to see the potential in us. To encourage us. To invest in us. To help us balance our work and life.

But can you do that for yourself?

That was my challenge to myself. Job or no job. I would be the very best boss of my own life.

Here are the 4 things that I found make exceptional companies or bosses:

1. Investment in Professional Development

This is a benefit that I see others greatly appreciate receiving from a company, yet have the hardest time giving themselves. You have a boss or company that sees a lot of potential in you so they: send you to a conference, provide you mentoring, give you a training course, create a development plan, offer continuing education. That is awesome!

But it is SO hard for people to invest in themselves!

Our culture has this narrative that says: It’s a great idea to spend $40,000 going to college and use 4 unpaid years of your life doing so. BUT then it’s crazy to spend ANY money to continue growing and leanring……unless it’s another $40,000 for grad school.

Um….this seems bizarre to me.

It’s something I have had to push back against for myself and I see so many people struggle with. If your company paid $1000 for a conference, retreat, training or mentoring, you might think, “That is a smart investment they made in me!” Or even, “Well, it’s about time!”

I had a huge shift in my life when I choose to invest in myself. AT LEAST to the same extent that would be reasonable for a company to. It boiled down to deciding that my life was worth investing some time, money and energy into. 

If it would be a smart investment for a company, I would argue it’s a smart investment for you.

Here is my new litmus test: If I would be crazy excited about an opportunity (if someone else is paying for it), then I ought to consider paying for it myself. For example, I would be bored to tears going back to college, but psyched to attend a cool conference or small retreat with other creative entrepreneurs. So I should seriously consider and pursue these types of opportunities.

2. Positive Encouragement

Three years ago I made a commitment to not say anything to myself that I would be upset if another person said to me.

A great boss notices the good work we do and gives helpful feedback in areas where we can grow.

If I was going to become my own Best Boss Ever, I would only say things that were helpful to growth or encouraging about myself. It’s estimated we think about 20,000 thoughts a day.

I challenged myself to shift the percentage of thoughts that were useful.

Unhelpful thought: “I’m just an idiot about (this topic). There is no way I can do this.”

Useful thought: “Looks like I might need to schedule a few more hours to figure this thing out than I had expected.”

Talking to a lot of successful and happy people, I find they have a high percentage of helpful thoughts.

3. Work/Life Balance

We love to work for companies and bosses who help us protect our work/life balance. Going into this Work Optional life, I knew that would entirely fall on my shoulders.

If you are an employee, you can still set boundaries. How late you respond to emails, when you take calls, making sure you actually use your vacation days. Not every boss will do this for you.

Oddly, it can be even more challenging if you work for yourself. If you have clients, it’s can feel like you have 20 bosses with sometimes unreasonable expectations.

One of the benefits of becoming financially independent even if you love your job is being confidant to set better boundaries.

As you grow in your financial freedom, you get to learn to be your own Best Boss Ever and write your own rules. One rule will be what kind of stuff you want to do and how much.

4. Great Community

All the amazing places I worked had positive and supportive work environments. Like minded people working together for common goals. If you have this in your 9-5, it’s often a really rewarding part of the package deal.

In becoming my Best Boss Ever, I decided to create that for myself.

You can seek this out in faith communities, non-profits, hobbies or professional relationships.

Over the last two years I have spent time, energy and money investing in curating my own hobby/professional community. The really cool thing, when you take this responsibility into your own hands, is that you can pick from a large pool of people. I have been able to build relationships with the most creative, interesting and inspiring people I know in this personal finance space. Just knowing them has made me better.

In being your own Best Boss Ever, you get to pick whatever space you want to invest in. And that means you also get to pick the people. It can really be as simple as showing up online or in real life and offering to help. A little relationship tip, the best relationships are built on generosity.

Become Your Own Best Boss Ever

It’s easy to complain about bad or mediocre work environments. It can be easy to keep searching for the next and better boss or company. Instead of looking for the next Best Boss Ever, start to practice being that boss for yourself now.

Send yourself to a conference. Create your own professional plan. Only give yourself helpful feedback. Set some work boundaries. And invest in a dynamic, interesting community that brings out the very best in you. It’s hard for others to see your value if you don’t see it first.

And if you need to, buy yourself an aspirational mug to keep you on track.