How to Self-Employ
I had a friend that used to talk about “how to summer”, I loved it. It gave me the sense that there was a skilled way to “summer” and an “unskilled” way to summer. She would summer well, like the best summering ever. She had a boat, a lot of great swimsuits, a huge endurance for partying, and there were seafood bakes and boils. It was so skilled! I tried so hard to “summer well”, but I never really got the hang of it. I was living in New York City at the time, so one might say summering well has its limits or at the very least, has its very own special interpretations, and I had limits. That might be going to the Hamptons - the epitome of summering if you buy into the social currency that it sells! But I didn’t. I found the drive to be awful, the socializing stifling, and where are the beaches?! I went to a beach only once. I went to brunch so many times though. Was that summering? Didn’t feel like it. It felt like I was getting drunk during the day and eating breakfast too late. I like to eat blueberries, which feels like a good summer thing, but I can’t sit out in the heat too long. I get dehydrated really fast, and I get too hot. It doesn’t seem like I am good at summering. But, I am, I guess, if you loosen the reins of what good summering looks like. Anyway, this post isn’t actually about “summering''. It’s about how to self-employ.
The idea was brought up by my husband who said to me one morning “you need to learn how to self-employ”. He didn’t say this to be critical. He said this because I had spent the morning telling him all the realizations I’m having about how I over-complicate things, and all the complicated ways I was going to fix everything. I was so confident in telling him that my plan was to simplify, get down to my essence, and plan to stop over-complicating all of it. I would do this through employing some pretty complex measures - mind-mapping, re-thinking my website offerings, setting up a different business model altogether, using my time completely differently through simultaneously loosening my control over time AND tightening my control over it! And I wasn’t even joking. I would start to stop things. I would not swim as much, because that seemed complicated. I would not go to my health and well being classes because I was over-thinking when I went, and scheduling them was hard. And so, my big plan was to untangle everything to let go of the distraction of doing those things. I would sit down and make a whole new plan. Think more. Re-design it all. Really get it all worked down to its core and essence. And…why is that so wrong? It’s not. At all. BUT. I have been overwhelming myself trying to get the right structure, offerings, cadence, and schedule. It’s a thing. And, it’s a thing I felt I was failing at because I couldn’t keep my own time and activity commitments. I couldn’t get everything where I wanted it to be. I still haven’t, by the way.
Why is this of note? I mean, it’s not really. It’s a woman struggling with how to manage her time, business, and what she wants to be offering to people as well as herself. But, it’s a common issue and actually that’s why it’s of note. I imagine I’m not the only one who is struggling with “how to self-employ”. I worked in a very structured environment for many years - by structure I don’t mean regimented. Actually my days were absolute chaos. But, the structure that was there was twofold: 1) I knew I had to sit at my desk for 10 hours, and 2) I knew I had to do what other people told me was important to do. Neither of those things are true for me anymore as I quit that life to start a new one. Now, I am the one who decides what’s important, how much time to spend on it, and what happens for me day to day. It’s daunting. It’s not as liberating as I thought to have so much say in my own life…I feel everyday I’m not doing it well.
Of course, I have done the sensible thing and endeavored to read and learn about time management. I have spent a lot of time seeking the truth on how to structure my days as a self-employed. I have read that I should plan my week, time block things, be disciplined, and make sure I do things, anything! Imperfect action is better than no action, I have read! I love that because my special interpretation is DO THINGS, ALWAYS, ANYTHING, ALL THE TIME, BE BUSY. Yeahhhh, that feels like what I’m used to, I can do that!
Now, the joke is, I don’t think they mean it like this - I don’t think keep yourself super busy is the point. It’s merely a nod to the fact that as a self-employed you do need to implement some structure and have consistent work habits. But, I am having a problem with this because I take it to an extra level. I am extra, while also being super basic (I am not sure if this is a thing anymore, but I am, so..). I do what I’m told in these articles, I take them literally, I take action, like so many actions, and they’re so imperfect it’s almost cute. I set up so many time blocks on my calendar that you would see it and think I’m the busiest woman in all the land. I see the reminders come up and I groan. I look at my self-made calendar schedule in the morning and I think “how am I going to get all of this done?!” And, then…I don’t, I don’t get any of it done. I brush off my calendar invites! I skip out on myself! I deem my own meetings a waste of time! I ask myself - do I really need to be there, am I critical? I’m not. I treat myself like one of the people who used to send out too many meetings in the corporate world and I ignore that person. What the f*ck, right? It’s weird. Then, I get down on myself because I don’t follow through with the meeting I set up for myself.. I fret. I think about it all day. I could’ve just attended that one hour meeting with myself and been done with it. I didn’t though, because I didn’t see the need to. And now I’m spending hours trying to reschedule with myself.
BUT, I was taught a long time ago that structure is the most important thing - set up my time, decide what I will do, and then be disciplined about doing it. I do agree with this actually. I have in large part set up my core business offerings around this very idea - structure ideas and concepts so that we can have simple and clear actions. Take time to analyze what we need to do, so we can ensure we are doing the right enough thing. I believe in this. But, it’s gone awry for me in my own treatment of it. I have applied it to everything, and that’s just not good. I have mistaken over-booking my time as structured. Sitting at my desk all day thinking of work for myself to do? Yes, please! I love that because it feels familiar. It feels right because I’m working, or acting like I’m working! But, is it right? No. It’s not, that isn’t time management or structure. I chose self employment so I wouldn’t have to do that! Why am I forcing myself to? Because I’m used to it.
How to self-employ well is going to look different for each of us. We may in fact need to be at our desk all day, on meetings. We may in fact need to run around all over the place meeting with vendors, looking at production, or doing all the things. It’s the nature of small business. BUT, what I have come to recently is that there is an inclination to over-do things, simply for the sake of doing things. We want our businesses and our lives to thrive and we interpret getting to that point by WORKING A LOT. Even if the situation doesn’t call for it. We have thrown intentionality overboard in a lot of ways, and this is creating the feeling that we are productive - because although we aren’t intentional we ARE doing things, and eventually one of those things will bear fruit, right? I am not so sure anymore and so I challenge this - for myself and for you. Here are some things I have been working on and asking myself:
Am I being intentional with what I’m doing? The only way for me to know is to be clear and calm about why I’m doing something. This should map to the big picture. For instance, my purpose for starting my own business was to have flexibility - both in the time I have and the work I decide to do. If I am booking my time back to back and taking on work I’m not really so bought into, how is this mapping back to my true intention?
Am I doing things out of habit or out of necessity? This isn’t so different from my question about intentionality, but it can get me to a different place since the question is asked in a different way. Am I sitting at my desk all day today because I need to, to fulfill my core intention, or am I sitting here today because I am in the habit of doing it? Often it is the latter and this is a wast of my time, I have come to realize.
What do I need to spend time on? This one is tricky because, as a small business owner, I need to do a lot of things. There’s nobody else who is doing them. BUT, the key to this question for me is, can I accomplish this thing is a more efficient way than I am now? The answer is almost always, yes. How do I figure out how to make it more efficient? I go back to the top and ask myself what is my intention for doing this, is it necessary? I can get pretty efficient when I’m clear that the answers to those questions are YES. When I’m not clear on the yes, actually, it’s pretty obvious because I spin and doddle. That’s my big tell.
What do I need to be consistent about? Consistency to me is the key to everything, but here’s the catch - not all things need to be consistent. I have new clients coming in all the time, and I spend a lot of time figuring out who they are and what they need. This is not going to be consistent, because every client is unique, BUT what can be consistent is how I get to that information. I don’t need to reinvent the wheel for this process every time. What else is there, like that? More than I would have ever imagined!
The bottom line good news here is that “how we self-employ” is a thing in and of itself. If we look at how we are using ourselves, the habits we are perpetuating, the constraints we place on ourselves, we have a lot of opportunity to re-shape them. We have all we need to build and run our business in the way we wan if we are intentional about how we do it.
