Are you being a horrible boss...to yourself?

In the July 2025 edition:

• How to stop being a terrible boss…to yourself 🙃

• “Time poverty” and its effect on your well-being ⏰

• A recipe for a nice, cold treat (because it’s hot af outside)

SOMETHING USEFUL

Are you being a horrible boss…to yourself?

Back in my corporate days, I had a lot of shitty bosses. Decent ones too, but mostly shitty. It’s one of the main reasons I decided to quit my job at Google and start a business. My experience working for other people was so frustrating, it was pretty much guaranteed that I would be better off managing myself…right? Right?!

But as time went on, I noticed something. I was doing some of the same shitty things to myself that my bad bosses had done to me in the past. Things that, if they were coming from someone else, I’d be complaining to my husband about it over dinner every night.

Today’s article is about recognizing self-inflicted bad-boss behaviors, so you can put an end to them before they wreck your motivation and hurt your business.

Denying yourself opportunities to learn and grow

One boss I used to work for was deeply anxious about how he was perceived by his boss, which translated into trust issues with his team. He never let any of us try something new because he worried our potential mistakes would make him look bad.

We all got frustrated as our skills grew stagnant and all the interesting, complex projects were being done by senior leads (who, in turn, were so bored working on stuff they could do in their sleep.) No one was happy, no one was learning—it dragged the whole team down.

So imagine my surprise when one day, I realized I was doing the exact same thing to myself.

Here’s what happened: I’d recently had an idea to pitch a partnership with a local small business support group that also served my target clients. It was out of my comfort zone, but logically I knew it would be a direct way to introduce myself to potential clients, share useful information with them, and make new connections.

An interesting, complex project? Yes. One that could help other people and be great for my business? Yes.

So what did I do? Nothing. I was nervous the pitch wouldn’t go well, that it would be “weird” somehow (??), or that I’d end up committing to something I didn’t really want to do.

That’s right: I was anxious about how I would be perceived and what could happen if something went wrong. And I was using that anxiety as an excuse to deny myself the opportunity of even trying. Just like my shitty boss!

This realization hit me hard—I would have been PISSED at a boss for doubting me like this. Now, when I feel reluctant to follow through on an idea, I ask myself if my uncertainty or anxiety are blocking me from a growth opportunity. (PS: I did pitch the partnership, and it’s in the works ;)

Underpaying yourself

This one is more complex than it initially seems. On the one hand, it’s important to pay yourself appropriately so you can meet your needs. On the other hand, owning a business can provide non-monetary value—not dollars that put food on the table, but flexibility, purpose, or autonomy that allow you to live the life you want.

In my corporate job, I was paid very well but all of my time belonged to the company. This was fine until my son was born, then suddenly it was unbearable.

Now, as a solo business owner, I make less money than I used to but I have far more control over my schedule, more flexibility for parenting and self-care, and complete authority over what I work on. Those are valuable assets to me, and I’m willing to earn less than I did in my corporate career in order to have access to them.

Of course, I pay myself enough to cover my needs, but I don’t sacrifice my autonomy for more money anymore.

So when you think about whether you’re underpaying yourself, especially if you’re comparing your self-employed pay to a previous job, remember to factor in the non-monetary benefits you’re receiving.

And if you’re reading this and thinking, “What benefits? I’m working around the clock with no time for anything else and I’m still underpaying myself!” you’re absolutely not alone. But maybe you’re being an unfair boss to yourself. (If this is you, I’d love to chat about making your business work better for you.)

Completely disregarding your boundaries

These are a few ways my past bosses trampled on my boundaries:

• Expected me to work while I was on vacation and on most weekends

• Messaged me incessantly at night while I was nursing my baby

• Forced me to plan team events even though it wasn’t part of my job (and I’m really bad at it)

• Put early-morning or late-night meetings on my calendar without a heads up

• Volunteered me for tedious or menial tasks without asking (yay for being a woman in corporate America)

There’s more, but you get it. The message I got was, your time and energy are ours and we will use them as we see fit without considering the impact on you. Eventually I got that message so fully and completely that I quit.

But now, as a business owner and boss of myself, I’ve done some similar things. I’ve over-scheduled myself, given myself impossible deadlines, forced myself to work during off hours, and committed to tasks that I’m just not suited for.

I’m proud to say I’ve improved in this area, but there’s always more work to do. I’ve gotten better at limiting the hours I spend in meetings each day and giving myself enough time to work at a comfortable pace. I rarely work in the evening anymore. And you certainly won’t see me organizing a two-day offsite for 30 people ever again.

So think about your boundaries around how you use your time, energy, attention, and even money. If you’re not sure what your boundaries are, start by defining them. Your business is just one part of your complex life, and the other things that are important to you deserve your time and attention, too.

Let’s stop doing this to ourselves

At their core, the reason shitty bosses are that way is that they don’t care much about the humanity of their employees. Instead, they see them as cogs in a machine or sources of potential problems—something to be controlled rather than supported.

As business owners, we should not and cannot see ourselves this way. We need to recognize our humanity, give ourselves grace in the face of challenges, support our own needs, and set ourselves up to grow and reach our potential. Even if we make a couple missteps along the way.

SOMETHING NEAT

One of my biggest sources of work stress is feeling rushed, like I have too much to do and not enough time to do it (I know, join the club 😂) The issue is, I also struggle with procrastination, which means I often create this stress for myself (see above article).

So I found this article from Techno Sapiens to be super helpful with both defining the problem and understanding the negative impact that my procrastination-induced “time poverty” has on my well-being. Putting some structure and terminology around this situation has helped me pinpoint specific ways I’ve been wasting time, so I can start using my time better.

Now, my goal is to increase my “time affluence” so I can stop rushing, and stop stressing.

A LITTLE TREAT

I’m not a hot weather person, so I need a lot of cold treats to get me through the summer. One of my favorites to make at home is Smitten Kitchen’s Key Lime Pie popsicles. Ridiculously tasty, and the hardest part is waiting 5 hours for them to freeze.

Enjoy!! (Seriously, how is there not a popsicle emoji?)

WORK WITH ME

This newsletter is for everyone, but a one-on-one consulting engagement is tailored to you and your business. Here’s how I can support you:

• Strategic Action Planning—For solo business owners with a lot to do, and never enough time. We’ll refine, prioritize, and organize your goals, and I’ll create a road map for you to get them done. (My most popular service, now scheduling for September/October.)

• Resilience Jumpstart—Turn analysis paralysis into decisive action with affordable 1:1 support to get you moving in the right direction fast.

• Operations Analysis—Is your business built on a strong, long-lasting foundation? An operational deep dive will reveal opportunities for improvement, and tell you exactly what to do to make your business more resilient.

• General Consulting—Get expert support with business challenges like workload sustainability, financial fundamentals, pricing, client communication, and more.

When you’re ready, schedule a free 30 minute intro call with me.

Thanks for reading—see you next month. If you have a business owner friend who would find this newsletter useful, please share it with them!