Being the boss lady. – Modern Mrs Darcy

School started two weeks ago around here. Even though my kids aren’t starting until after Labor Day, we’re in transition mode, thinking through what we want our fall routines to look like.

We have a lot of pieces to put in place. My husband and I both work outside the home (though my hours are minimal at this point). We homeschool our kids, and manage their extracurriculars. My self-employed gig—as a writer and blogger—is begging for more time.

Right now, we’re thinking through what kind of schedule we’ll keep and what kind of help we’ll need. About two years ago, when Will went back to a more-or-less regular 8:00-5:00 job, we started hiring regular help for things like childcare, laundry, and homeschool assistance.

And I’m getting some help with the blog, too. Will has always helped with the back end; now I’m thinking through just how much photo processing and technical stuff I can outsource. Additionally, I’ve got a redesign in the works and bigger projects that could use a helping hand.

It’s become clear to me, as we think about hiring people for this season, that being the boss doesn’t come naturally to me. I’m not even good at being my own boss some days. (Honestly, I’m kind of hard to manage: I fly by the seat of my pants, dread decisions of any sort, and don’t cut myself enough slack.)

I’m not good at asking for what I want from people. I’m not even good at knowing what I want from them.

I suspect this has everything to do with personality: as a recovering people-pleaser and an enneagram 9, I don’t feel cut out to be the boss lady.

I read a book this week (that one of you recommended—thank you!) called Creative You: Using Your Personality Type to Thrive. It’s about bolstering your creativity by learning more about your personality type, but I found its insights helpful as I think through what kind of structure will best suit us in the coming year.

The book is centered around the Myers-Briggs personality types. I’m an INFP: the idealist, the healer, the muser.

I highlighted the heck out of Creative You, because the author nailed my type.

As an Intuitive (N), my strength lies in exploring possibilities and finding relationships between seemingly random things. I’m good at taking the long-range view; not so good at the details.

I’m an excellent starter and a horrible finisher. The authors put it well: NPs are “an endless lightning storm of ideas, but the bolts don’t often strike the ground.”

I can dream up 1000 ways to approach a problem, but am horrible at deciding on The One Way to move forward. And when I do decide, I do it slowly. I need lots of time to mull things over.

I seek harmony, dread controversy, and hate telling people what to do.

In short, I shouldn’t be anybody’s boss.

But I’m in a position where I need to be.

I knew all these things about myself, but seeing them in the book in black and white was so helpful, if more than a little sobering. I was reminded of why I struggle so much with being the boss lady—but why it’s so important that I do so. I need the help, especially from people who aren’t like me.

Reading the book, I was reminded of how much I’ve learned about managing myself, and others—even if I don’t always put it into practice.

As far as managing myself, I’ve learned that:

• I do well with schedules and routines, even though they don’t come easy.

• I need deadlines. I love deadlines, because they help me follow through.

• If I wait until I feel 100% sure before I make a decision, I’ll miss the opportunity to make it.

• All the good intentions in the world don’t get me anywhere unless I have a plan for following through.

• Even though I work for myself, I need grounded, detail-oriented people on my team—friends, employees, colleagues—to talk things through, help me figure out what I need, and keep me accountable.

As far as managing others, I’ve learned that:

• It’s important to ask for what I want from the people I’m managing. I’ve heard smart women leaders say this is often hard for women to do. It’s definitely hard for me.

• In order to ask for what I want, I have to figure out what I want, remembering that I’m not going to feel 100% sure about what that is. (See above.)

• I shouldn’t apologize for asking people to do their job. This is ridiculously hard for me. Like, I-should-talk-about-this-in-therapy hard.

• I need grounded, detail-oriented people on my team—designers, accountants, homework checkers—to notice the details, catch my mistakes, and help execute on the follow-through, whether that’s for a blog post or my daughter’s math homework.

(I’m very curious about what these lists look like for other personality types.)

In thinking through my conflicted feelings about being the boss, I’ve realized how many of us take on that role sometimes, even though we don’t think of ourselves as being such. I’d love to hear about your experiences with being the boss lady (or boss man, of course), and welcome any tips you have for being a better boss. 

P.S. 35 things I’ve learned in 35 years, and self-awareness makes everything better.

P.P.S. I wrote a book about personality! In Reading People: How Seeing the World through the Lens of Personality Changes Everything, I walk you through 7 different frameworks, explaining the basics in a way you can actually understand, sharing personal stories about how what I learned made a difference in my life, and showing you how it could make a difference in yours, as well.

Books mentioned in this post: