Become Your Best Boss Ever

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.


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32 thoughts on “Become Your Best Boss Ever

  1. A few years ago we started taking courses for fun. It was hard to swallow the cost, but we have LOVED the information and the results. It’s a tricky line to walk, spending thousands of dollars, but it has absolutely been worthwhile (thus far!).

    • It can be such a hurdle! I never want people to go overboard, but most of us struggle on the side of being too cheap with stuff that matters most. My basic guideline is 1% of your salary, 10% of a raise or .05-1% of your net worth (at least as much as your investment fees!) Our personal growth should be worth at least that much. Once we start seeing a good ROI, we can grow from there.

      And often the growth we see in one area translates to growth in other areas of life. It’s not for vanity that so many entrepreneurs and leaders work out consistently or hire personal trainers. That physical challenge gives them more energy, and mental strength in their work.

  2. Love this! I strongly believe that if you plan to develop yourself “differently” (e.g. Financial Independence, or anything else for that matter) than the majority around you, the key skill you’ve got to unlock is to become an autodidact (a self-taught) person. Besides money, you also got to invest some time and discover how you learn the best and allow yourself more relevant exposure in order to upgrade your desired skill-trees in whatever area you deem necessary. Learning how to learn and then knowing which way to go – unleashing your full potential. Leading your way. Being your best boss! Great post!!! Thanks Jillian

    • I love the part about being self taught and learning how you learn. I’m ready the Gretchen Rubin book right now, The Four Tenancies. It’s an interesting perspective on how people find their motivation. Once you understand that part of yourself, you can really lean into what works and make SO much more progress!

  3. Love the unique perspective, Jillian.

    I have trouble investing in myself too, and it’s really interesting to look at yourself the way an employer would.

    I know for me, a big part of the hesitation comes down to not wanting to get ripped off. There’s no limit to the number of snake oil salesmen who will sell you on “investing in yourself” with their subpar conferences/training packages/whatever scheme. I think the takeaway is that employers invest in reputable education for their employees, so there’s no shame in doing the same for yourself!

    • That use to be a big struggle for me too! Here are two perspectives that I have used.

      1. Pick things that are super low cost/ high ROI, like books. I started out by just buying books that would help me be better at my job. It’s hard to go wrong with a $12 book. But even that I would have coworkers who would say they would never do such a thing (and we worked on commission! So we literally earned more money based on our skill set!)

      2. I learned to diversify. Not everything will pan out and be a great ROI, and I had to learn to be ok with that. It’s like the stock market, not everything goes up every year, but if enough stocks grow enough, you still end up ahead. So, for example, I might buy 10 things for $100 each. 3 will be a total bust. 4 will break even. And the other 3 will give me 10x or 100x my investment. So I’m up at least $2000. It took me a LONG time not to freak out about the 3 things being a bust and learn to see the big picture. We naturally hate wasting money. But that fear can also cause us to avoid the things that would end up giving us great returns.

      So start small, and diversify. =)

  4. “our doubts are traitors and make us lose the good we oft might win for fearing to attempt.” – shakespeare

    i just wrote something related in looking at the qualities of honesty, capability, and fearlessness. the capability part can and should be developed and cultivated. a no money down investment is to take your valuable time to try and learn or develop a skill. it’s a cost just like money but worth it if for nothing more than to be a more diverse and interesting person. if you can trade that skill for money it’s also a nice cushion if times ever get tough.

    • Ohhhh, I love that quote! It’s so true. And I think your point about learning a skill is so good! Having a few difficult to master skills in your back pocket is a great way to earn extra income if you want or have something for a professional trade.

  5. Love this! And I think even if we aren’t in a work optional/mini-retirement situation, we can all do this to varying degrees. Learning to invest in myself and work on myself has been HARD, but it has also been so, so, so worthwhile.

    • Oh, absolutely! Maybe I should have made that more clear…. I think there are ways to start small, but it’s just a matter of getting the mindset right and getting started. I do this in all areas of my life too, not just professional. Marriage, kids, relationships, I’m always trying to learn and grow. =)

  6. Yesss! I never thought about self-love from this perspective, but that’s really what being a good boss to yourself is like. It’s treating yourself with the kindness that you give to other people.

    • Yes to your point, especially in the self-talk. I’m always amazed at what mean or unhelpful things people will think about themselves. It’s simply not useful to accomplishing their goals. I really believe we need to treat ourselves as well as we expect others to treat us, because we set the tone in those relationships and teach people how to treat us. I’ve seen a few employees start taking themselves more seriously as professionals and it seems that everyone starts to notice. =)

  7. Investing in yourself is probably one of the best things you can do. I’ve been focusing on this lately. I’m currently taking a blogging course to help boost my “business” next I’m going to focus on the finance side and improve my technical skills. It’s funny, I hated school when I was in it. Now I can’t get enough. There’s something to be said for learning what you want to learn.

    • There’s something to be said for learning what you want to learn. This is SO true! Which is why it’s great when people find work in areas they love. We have so much more potential to be successful at things that are in our natural skill set and that we love. I’ve seen so many people waste years of their life doing things they weren’t particularly good at and didn’t love. And good for you for investing a bit of cash into your blog! I know it’s scary at first.

  8. The positive encouragement thing is big for me. I probably call myself an idiot 10 times each day. I know I don’t really mean it, I’m just self-joking, but I’m wondering if it’s still a habit I should change. I need to try harder!

    • My litmus test: if you would be pissed off if your boss said that 10x a day “jokingly” (and I would be!) then you should stop. It’s just not useful. It takes a lot of work to change our thought patterns but it really is worth it! Because there might be a lot of challenging, brilliant, and inspired things you might do at work, that no idiot would do! And honestly, if you call yourself that enough, it’ll shape your behavior.

      It took me about 6 months of a lot of effort. But I literally never think anything unhelpful about myself anymore. Not about my appearance, abilities, relationships, ect. I don’t lie or feed myself fluff. If something is hard, I’ll say it’s hard. If I’m still learning, I’ll say that. But never crap just to tear myself down. And because it’s so weird for me to hear unnecessarily negative things, I don’t let others get away with that either for me or them. I’ve literally stopped conversations mid-sentence and said, “Hold on, what did you just say about yourself?”

      Although sometimes I am still sarcastic, but in a positive way. If I look like hell, I’ll think, “Well, I’m looking extra lovely today!” =)

  9. I agree big time with needing to continue to develop yourself professionally. I’ve missed two conferences over the last 6 months that I always enjoyed attending and always learned a lot from and I’m feeling it. I’ve just started looking around at different things I can attend to start working on myself again, without getting an MBA 🙂

    • There is some odd part of the US culture that says it’s ok to spend a small fortune on college but crazy to spend on anything else. I kind of get where it comes from, but I just don’t think it’s true anymore. There is so much good stuff out there! I’m a big book fan, but am still amazing at the sheer generosity of authors! So much work and knowledge, so blasting cheap. =)

  10. I’ve struggled with investing in myself for the first stage of my professional career, except for buying myself books and doing things that were free. But it’s true in this instance that you get what you pay for, so it get the best investment in yourself, you will likely need to invest money into it.

    Also, one thing that I think many people (myself included) miss is that you need to invest in yourself before you becoming an entrepreneur and while you still have a job. You need to be the boss of your life even if you still have a 9-5. It will give you more confidence and ability to handle important tasks, and one day if you make the jump to self-employment, you’ll be better prepared for the ride.

    • I think books are a great jumping off point! But once we start to see a little ROI there, it’s time to slowly grow into other areas as well. And I 100% agree in investing in ourselves before self-employment for about 100 reasons! Most things take time to learn, grow and scale. All those things are easier to do when your job is giving you good cash flow and a long runway! If people have a hard time spend $1000 when they have a $1000 extra cash flow a month from a 9-5, it will be near impossible when their business is running $1000 short a month.

  11. Wonderfully inspirational post Jillian! Each point is spot on, I keep wanting to point out one of the four points as speaking to me most, but then wanting to call out a different one too. Then I realized that all four are just so powerful and you already arranged them for me! Thanks!

    • Ah, glad you liked it! All four have been big areas of growth for me. And they have all made a big difference in the direction my life headed and the progress we have made. Plus I talked to so people and I after a while it’s rather easy to see that everyone either needs to work on one of these or has made awesome progress and is killing it.

  12. Personal and professional development is something I’ve been contemplating as I’m heading in to my own business. It’s a critical area no matter what line of work and I have seen the difference a conference can have, especially since at this moment (hopefully not too many more) I am working at a place that does not offer or encourage professional development. I am sure there are many free resources and I plan to look into them. Perhaps I’ll get a blog post about it myself 🙂
    Thanks for the thoughtful piece here!

    • Personal and professional growth are so important! I really like all forms: conferences, retreats, masterminds, online courses, sometimes in-person courses, accountability partners, mentors, local support groups. There are SO many things out there at every price point and time commitment. It will be really critical if you become self employed! I would start laying that foundation now so you have everything in place before you make the leap. =) Best of luck!

    • I’m always slightly amused when people say they want to be self employed so they have lots of free time, flexibility and travel. Those things CAN happen, but it’s not automatic! In someways it’s harder to vacation, but part of me still wants to be online. It much harder to walk away from my own work vs an employers work while we are on vacation.

  13. I hadn’t considered the “invest in yourself” idea outside of college. The idea of spending even a couple hundred dollars outside of college seems nuts (and even having my company pay for it, it seemed expensive for my required continuing education. Ha)

    • It’s such a common block for people! If I were to go back and redo the last 15 years I would spend 30% less energy on frugality and optimizing what I’m already know, and applied all that time, energy and money towards investing in my personal and professional development. Beings I’ve attended 30+ retreats and elective conferences, taken extra classes, courses, hired people, read 500+ books: I’m sure I did a bit above average. But I would still up that another 30% knowing what I know now. The ROI is huge in most areas, career/friendships/marriage/money mindset.