I was thrilled to close a new client recently (excited about the assignment, the point of contact, and the scope). In a past life, closing a new deal meant immediately going to Slack and posting an update, getting a little thrill from all the positive emoji responses. This time, especially since Jeff was out, I looked at my two elderly toy poodles and decided it wasn’t even worth it to try and explain either consulting or capitalism to them. I debated giving myself a high five but settled on opening champagne at the end of the day.
I left my “traditional” job a year ago this week: it was a bad fit for a host of reasons and I have no regrets. While I initially thought I’d take a little time, write a little more, and go back into corporate, I started to think more and more seriously about going out on my own.
Some things made the decision easier: I interviewed for several jobs that sounded terrible! One where, over the course of three interviews, I realized I was being hired to lay off 40% of a team and then “boost morale.” One where they contacted me with no job description and made me deliver a presentation with minimal context while I had Covid because it would be “too hard to reschedule” (no clue what I said because when I hung up, I realized I had a fever of 102.7 and spent the next two days in bed). One where I realized it was definitely not the right job for me about 5 minutes into the interview and then after 15 minutes, we lost power in a storm which I took as an actual sign from God to move on.
Those experiences were more than enough to give me the perspective I needed. And truthfully, building my own thing carried instant appeal: if one of my biggest complaints in past environments had been working for or with challenging and/or incompetent people, I was about to exclusively work for and with the best and most competent person I knew: myself.
But over time, I’ve learned that even I am annoying.
This may not come as a surprise to some of the friends and family members and former colleagues who read this, but I was shocked.
If I represent 100% of my employee base, then 100% of my organization likes to overschedule me, doesn’t maintain clear boundaries after hours, and never wants to do the work that I hate to do. Worse, I can’t delegate that hated work to anyone else because I am the only person to both assign and execute the work. It’s like being in a group project where you are simultaneously the organizer, the overachiever, and the dud who doesn’t contribute.
I’ve always gotten a lot of joy from working with others, which is maybe why I’m still surprised that, for all the control I have over my work and my schedule, so much of what I need to do runs through people who aren’t me. There’s a lot of “oh I have to introduce you to Gretchen,” and then I email but after two or three follow-ups, I just move on, and I never meet Gretchen, and maybe that doesn’t matter, but maybe it would have been helpful. I’ll never know.
Or someone will say “let’s connect next week” and then I send times because I know I’m more flexible, but then they don’t reply. I’m constantly walking the line between being persistent and annoying, feeling like the former on my most empowered days and like the latter on all the days I’m full of doubt and googling “positive affirmations for when people ignore you” and reading the first handful out loud like a doctor prescribed them.
The other side is being proud of work, or needing to workshop, or wanting to celebrate. I’m the only person with all the context on my business so trying to share with others requires a lot of background that often sends me down rabbit holes of frustration and annoyance. I spent six weeks completely rebuilding the methodology and the documentation of a large part of my work and I ultimately created a 50-page operating manual that I’m so proud of. And that milestone that would have been a major KPI in a past department and gotten listed as a monthly or quarterly “highlight” just goes in my personal journal as a “win.”
While I operate as a company of one, poor Jeff has been conscripted to be the unpaid intern in my LLC with such exciting responsibilities as looking at everything I write or make and telling me it’s amazing and then having to say “no it really is” when I accuse him of lying just to make me feel good.
In established corporate roles, I was able to assess progress and success by looking externally. Now I have to look internally for indicators that I made the right call. I do find them every single week but they’re far less dramatic. The same goes for celebrating: I may not have a Slack channel to post an update to but when I was able to tell Jeff about the client I was so excited to close, we decided it was time to pop champagne I’d been saving for an undefined “big win.”
The toast doesn’t fix it all. I can pick the good champagne flutes, but by the third sip I realized that there’s one job I can’t fill nor can I outsource. I can make Jeff toast the win (he’s happy to, although, to be fair, he’s just happy to toast anything) and I can make him read a 50-page operating manual. But I can’t vent to Jeff about my annoying coworkers anymore because that’s just me (although, again to be fair, he probably has his fair share of complaints about me).
Signs make it easier to gauge whether you’re making the right choice: a power outage in a bad interview, a well-timed lightning strike, some piece of biblical stage direction confirming I’d chosen right. More often, it’s the little things: champagne flutes I “borrowed” from my parents a decade ago, work moving forward, a poodle snoring in what should be my seat. And it’s a treat to toast my favorite coworker — the one who does everything the way I would do it, will never let me down on the group project, and is getting a little less annoying every day I work with her.
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