My BOSS AF planning method. AKA how I deal with the fact that I can never actually plan anything and it makes me want to give up on life.


I don’t know about you, but I THINK a lot about stuff that I’d like to do, stuff that I need to do, stuff that I have to do, stuff that maybe got done (?) or maybe didn’t, stuff that someone else should do (accountant, attorney, team member, client, collaborator, friend, parent, etc), and even stuff that I wish I didn’t do (that 2nd glass of wine).

But while I’m spending this much time thinking, I’m not actually doing. However I feel exhausted because my brain is not taking a break. It’s looping over and over and over. Hoping I don’t ‘forget to do anything’.

You know what I’m going to say here.

It’s unhelpful. And unproductive. All the guessing and thinking and worrying.

So, why do I do it?

I’ve not only gotten used to it (I practice it a lot so it comes to me pretty naturally) but I also have a thought that prompts it AND behaviors that go along with it.

Theres a trigger or two:

  • I’m the boss in a fast-growing startup in which there is always a giant pile of work + a giant list of improvements + a lot of people who are also daring greatly and need coaching and help tackling problems + a shit ton of stuff on fire threatening to ruin my life.

  • Things take longer than I plan.

There’s a thought (or a few):

  • “I have too much to do.”

  • “I’m forgetting something really important.”

  • “I should be doing something really important.”

  • “What will my team/clients/collaborators/customers need from me right now that I haven’t done yet?”

  • “What am I NOT doing right?”

  • “Why can I NEVER get to what I REALLY want to do?”

Then there’s a feeling from all of these thoughts:



Then there’s a set of ‘actions’ that I do when I’m feeling panicked / resentful:

  • Overthink about all the things I need to do

  • Have zero ability to prioritize what’s important

  • Have a glass of wine

  • Grab a snack

  • Jump right in and do ‘something’

  • Be annoyed with the people around me

And my results of these actions:

  • I ease short-term stress but add to long-term stress

  • I’m not really in the moment of what I’m doing. I’m distracted.

  • I don’t get better at being a CEO / boss

  • I don’t practice delegating or deciding or planning or even being ‘off the clock’

  • I drink too much wine and have too many snacks

  • I continue to believe I can’t take any time off because ‘there’s just too much to do’

  • My task list inevitably grows

  • I don’t ever get to the stuff that I’m thinking about a lot because other stuff usually gets in the way

  • I don’t make long-term choices that increase my happiness over time, I make short-term decisions that deliver me pleasure in the moment but that actually have a ‘net negative’

  • I’m kind of annoying to be around

So, how am I going to get myself out of this?

  1. First, I’m deciding to become aware of this.

  2. Secondly, I’m going to write down all my thoughts. (which I just did above)

  3. Third, I’m going to decide what feelings I WANT to have (committed, confident, resolved, boss-like)

  4. Fourth, I’m going to decide what thoughts I need to think to trigger those thoughts (“I’m doing this right.” “I’m a superboss.” “I’m really good at this shit.” “I’m the only one who can run this business.” “I’m here for a reason.” “I’m a cool-ass boss." “I live an incredibly creative, independent, cool-af life.” I run AN ACTUAL AMAZING BUSINESS.”)

  5. Fifth, I’m going to plan my schedule ahead of time AND allow myself to break my schedule but not to not create one to begin with (which is often what I do since my schedule is often interrupted by ‘emergencies’ from vendors, team members, customers, city officials, accountants, bankers, etc).

  6. ****In order to plan, I need to manage my mind in this moment, too.*** So, when I think about planning my schedule, a crucial step in this process, I often have a few thoughts ——-> 1. Why plan? You’ll get interrupted anyway. 2. There’s too much to do (see above). 3. But why not just get started and work on something NOW?! 4. You don’t have time to plan! You have too much to do!” All of this just contributed to my inability to plan shit.




7. I think to myself: “Brain, stfu. Planning is a thing only bosses do. Sure, I have a lot of cool-ass things I want to do in my life. And your inability to see that as a positive is really getting on my gd nerves. Yeah, I probably will get interrupted but who cares. This IS working on something now. Planning is actually an activity you dummy brain. Good try. I have time to plan because I want to plan and it’s my life and I’ll live it how I want to live it.”

8. And then I get on to planning. And I also realize that I might have to re-plan. And I’m just ok with that.

And because of my nephew interruption, I was actually able to put this into practice and then I decided to name it. So, it actually helped me be better at my job. Take that, interruptions. Take that.

This is what I call the ‘Boss AF planning method’ created in order to deal with a constant set of interruptions that are unplanned and uninvited and generally unpleasant while also being a total boss bitch.

How it works:

  • I plan my schedule.

  • Something interrupts me as I’m getting said item done.

  • Instead of weeping and feeling like giving up on everything, I think something different.

  • I think “Fuck, this sucks.” and I feel the disappointment that comes along with not getting to ‘do what I had planned.” I also think, “Oh, ok Universe. You’re gonna TEST ME, huh? Haha, well I WILL get my shit done, because there’s nothing I love more than a goddamn challenge.”

  • I give myself a few seconds to grieve the loss of my schedule and also want to punch the universe in the face.

  • Once that is done, I say to myself, “YOU are a superboss." I say, “Bend, don’t break.” I say, “You eat interruptions for breakfast.” I say, “Bitch- you’ve got this.” I say, “GAME ON.”

  • And because of those thoughts, I feel confident and resolved once again. Which allows me to close my laptop and re-assess my schedule- planning it again even though I had already planned it.

You see, I want to set my schedule once. But that is not my life. I want zero interruptions. But that is not my life. I want to predict my future and have nothing get in its way. But again, that is NOT my life. I wonder if it’s anyone’s life. If it’s your life you should just tell me so I can secretly study you and figure out how the hell you do it.

I do engineer moments I KNOW will be uninterrupted (super-early mornings, days when I work from home instead of at the office, Saturday mornings) but I also realize that much of my work is going to get interrupted AND I also am sick of being resentful of life’s interruptions PLUS not getting my most important work done.

In the moment of interruptions, I find ways to be a good human. I remember to breathe. I remember it’s ok to feel sad and disappointed. I usually ask for just one minute to feel my feelings, close my laptop and be present for whatever interruption is more important than this work.

Sometimes I don’t allow interruptions. Sometimes I allow myself to set a boundary around my time. I set expectations with others and gently tell them that this is not the time for me to spend with them and can they please write it down or send me an email or call me at at better time?

So, stick with it, bosses. You CAN do this. You, too, can have a life with other humans in it. With stuff other than work. While being kind to people and to yourself.

Sometimes shit does suck. Sometimes you don’t always get to do what you want. At the exact moment you want.

But also sometimes you do.

Stephanie Sheldon