Yes, You Still Have a Boss

Most people gravitate towards self-employment for independence’s sake. We’ll often chortle, “I don’t have a boss!” thrilled with the subversive pleasure of it all in a world that worships authority.

That’s the thing I find interesting about language– — the implications in word choice are immense. Saying instead, “I’m my own boss,” gets a lot closer to the heart of the matter but what often seems to happen is we become “our own employees.” Whoops.

A Management Vacuum

It’s one of those traps that sort of sneaks up on you. You hang out your shingle, and you get to work. You work and you work and you work, and suddenly you realize– who’s keeping track of strategic initiatives? Who’s even coming up with them? What’s the big picture plan here, and how do you know you’re making progress on it?

That person is you. Or ought to be, anyway. 

So yes, you still have a boss, but if you don’t realize the responsibilities of that role and make a point to discharge them capably, you’re going to be a really shitty boss. Not the kind of boss you gives you a hard time, of course– — just the kind of boss who doesn’t show up for work half the time and never knows what’s going on. A benignly shitty boss, if you will. 

So how do you get into the habit of being a good boss? By doing what good bosses do.

So how do you get into the habit of being a good boss? By doing what good bosses do.

Shift From Implementor to Visionary

God knows nothing would get done if you weren’t the one doing it. That’s pretty much the definition of solopreneur, and the reason we fall into the management vacuum trap. We have to implement, relentlessly, if we’re going to be in business. 

The trouble is, we also have to shift to big picture views, and that’s tough to do when you really have to maintain focus. 

According to Your Brain At Work, by David Rock, planning and prioritizing are the most resource-intensive things you can do with your brain. So you have to do it first, or you’re never going to do it. That’s how hard it is. 

That’s why I advocate weekly reviews. They’re basically the first step in learning to “be the boss” and practice that big picture perspective. The fact that planning is so resource-intensive is also why I recommend doing them on the weekend, when there’s no deadline pressure, and you’re well-rested.

Ask Good Questions

The problem with the Implementor mindset is that it’s simply focused on doing things. All it wants is to check stuff off the list. It’s not reflective, it’s reflexive. It’s not concerned with high level issues of whether a particular action is worthwhile, or the most efficient, or if it should really be put aside in favor of something else— it’s pretty much a mindless worker ant like that.

The job of the boss is to ask good questions. Questions like “What are our objectives?” “What have we learned?” “Is how we’re doing this aligned with our purposes and principles?” 

It’s about asking “How do we want the client to feel during every aspect of the process?” “How can we help the client feel more that way?” “What does our client want to accomplish and how can we aid them?”

It’s also about taking care of the goose that lays the golden eggs. The most important question in my weekly review is the one at the end: “Where am I at and what do I need?” and I reflect on my struggles and figure out ways to support myself better.

Schedule Times To ‘Be The Boss’

Being the boss is hard–even when you have no employees. So you’ve really got to make a point to schedule time to put on your boss hat. Figure on spending a couple of hours with your boss hat on every week, at least a day every month, and maybe as much as three days every quarter to do longer term planning. 

Put it in your calendar right now. 

Otherwise, you’ll get back into Implementor mode and forget. Dooooo eet.

And maybe ask yourself,

What do you need out of a boss?

CataLyst subscribers are currently enjoying a free mini-course to “Be The Boss” right now. Sign up to get it too!


14 thoughts on “Yes, You Still Have a Boss”

  1. Shanna,
    I’ve mentioned this before, but I put on my boss hat every Monday morning and plan the week out from a strategic and tactical perspective. That is, assuming I didn’t have the time or the desire to do it over the prior weekend, which happens from time to time.
    I schedule my boss time well, but I’m not a good boss yet because I don’t ask AND answer the right questions. You’ve noted a lot of skills and mindsets that get you to “good boss” status and I think you’re right on. I’m good at the “What have we learned?” and “Is how we’re doing this aligned with our purposes and principles?” type of questions, but need major strides with the “How do we want the client to feel during every aspect of the process?” and “How can we help the client feel more that way?” type of questions. Granted, I don’t have clients – just members of a community – but the approach is still the same.
    At the end of my day, the biggest question is, “Have I helped as many people as I could in all the ways I’m trying to help improve the world?” Many days the answer is no, but the number is slowly decreasing.
    I intentionally avoided positions in my decade in Corporate America that would have made me the boss of someone. But as a solopreneur, I wish I had the experience of being a boss so I could better put on and take off my boss hat.

    1. @joeyjoejoe That’s a pretty good question to ask yourself. It’s a great way to maintain the greater alignment of your life. Don’t worry about the other questions. Just knowing you have to do them is a great way to start doing them. It’s when it never even occurs to you that it’s hard 🙂 
      Maybe being a boss in corporate America would have taught you bad habits? I have felt bad for the people who went into management to ‘change things’. They usually wound up being the biggest victims of all.

  2. Well said, Shanna.
    I’ve never thought of entrepreneurship as working for myself. Some might not agree with that, but I don’t mean it literally. I am working for me, but it’s a separate “me” that wears the different hat. And I’m also working for customers/clients.
    There’s a section in The War of Art where Steven Pressfield talks about separating yourself from your work. Separate you- the artist from you- the corporation/boss. That helps you look at your business more objectively rather than make it personal. He also says he meets with himself every Monday, goes over assignments and types it up.
    If you’re going to run a real business, it helps to treat it like a real business.

    1. @deniseurena “If you’re going to run a real business, it helps to treat it like a real business.”
      Exactly. Sometimes I think people get too excited by the fact that “they get to come to work in their pyjamas” and forget that, even if you’re buck naked, the work still has to get done. It’s definitely good practice to keep your business separate from your sense of self… it’s too easy to fall into the trap of only feeling successful if your business is…

  3. Putting on my boss hat is something I need to learn how to do. As I’m just starting out, it’s really tough to balance all the administrative type stuff with the actual client work, much less add in this kind of higher-level stuff. But at the same time, I know how important it is and realize it’s probably easier to start doing it in from the beginning instead of pick up bad habits and then try to change them later 🙂
    I need a boss to help me see the forest. I get caught up looking at the trees sometimes. Goals more than a month or two away are overwhelmingly distant, and the non-boss me doesn’t really know what to do with/for them. I think the most useful boss function for me would be someone to sort of create a loose map of where I’m headed and how I might try to get there.
    It’s funny, the only times I’ve been the “boss” of someone else (bar manager, teacher’s aide) I haven’t enjoyed it at all. But then, those are sort of middle-management positions. Maybe I’ll like being the head honcho better 😉

    1. @remadebyhand It’s definitely a good habit to get into. Especially compared to the alternative… always saying “Oh, I’ll get to that when things settle down.” I always laugh when that excuse comes up. Even when i’m the one saying it…

  4. Scheduling times to “be the boss” has been a huge shift for me this year, and a very positive one. I’m great with coming up with lots of creative ideas, but I need my “boss” to help me filter through them and decide what gets implemented and what gets trashed. Now that I work for myself.. it’s gotta be me!

  5. Planning, prioritizing and may I add tweaking? It seems I am constantly tweaking which I suppose may be construed as byproduct of planning and prioritizing. It is fun to revise and refine until I have an item just right only to tweak it again a few months down the road. But really, I just like the word itself.
    It is baffling to read such a good post and realize that I never ever consciously put on my boss hat. I practice, I teach, I manage emails/calls, collect payments, but never think about about being the boss, although there is no question that I am.
    What could this possibly mean?

    1. @cjrenzi Without knowing anything about you, I would say that it’s because you’re not doing any high level strategizing, so the “bossly” activities are simply being handled without much comment by the Implementor side. 
      However, *knowing* you, I’d bet that most of that gets handled during your morning walks, or your coffee shop ritual. You simply don’t notice because it drifts in among other things, and it doesn’t matter in your case because you do have that luscious expanse of time– you’re not urgently trying to carve out the time and energy to do it.

      1. @Shanna Mann Ha! And good morning! How right can one be?  That’s exactly it. We (@Hoombah) simply are not feeling the pinch of management. I’ll tell ya though, carving out that time was a bitch. It took many years and a million coffees, walks and conversations to get here.  Thank you for your thoughtful reply!

  6. This is sooooo hard for me to do right now, and this week, being back home after 4 months, I’ve been avoiding being the boss like the plague. I was actually avoiding reading this because I knew what it would say, and I knew I’m not doing it. 
    One of the good things I have noticed is that as soon as I put on my boss hat and step out of implementor mode, things start to look and feel less daunting. The planning, even when it’s as simple as a to-do list, gets me out of “oh-my-god-so-much-to-do” mode. And the weekly reviews (which people would have a template for if they took our last permission slips class!) really make me appreciate how much I do get done each week. It’s becoming a favorite activity of mine.

    1. @sarahemily I am so excited that weekly reviews are a favorite activity of yours. I wouldn’t say they’re a favorite of mine, but I definitely notice when I don’t do them because I feel lost in the fog. But yes, pencil and paper planning are a must for when you enter freak-out mode.

  7. Pingback: The Sunday Subtext: Entrepreneuring Edition

Leave a Comment

Your email address will not be published. Required fields are marked *