The Shame Trap of the Self-Employed

The Shame List

People ask two things when they learn that I work for myself.

1. What’s the biggest positive? 

I get to work barefoot. (Also, my client relationships are awesome, the creative and professional freedom to choose my projects is marvelous, the knowledge I’m doing something that many people never have the nerve to do bolsters my shaky confidence, and the ability to work anywhere is a joy and a blessing. But yeah, I really love working barefoot.)

1. What’s the biggest negative? 

I’m enveloped by guilt. (Also, there are no guarantees of employment and I may lose everything at any moment, individual healthcare insurance costs an eye-watering amount and covers less and less every year, the loneliness and isolation is sometimes overwhelming to my already-depression-prone brain, and the work is sometimes so demanding that my brain hurts and my eyes literally cross.)

But the guilt. Oh, the guilt. Whatever I am doing, there are four other projects I could also be working on, sixteen personally career-building things I ought to be tackling, eight personal-life tasks to address, and about thirty-four personally enriching things that I will never, ever get to. 

Being my own boss means I am always juggling, and the juggling choices are mine to make. As a result, very rarely do I dive completely into a task without feeling like I’m letting something else go. I am guilt-prone and worry-prone. Irish Catholic, first-borne, highly-sensitive, distraction-prone, perfectionist, cancer survivor, ACOA, Type-A, etc.: I am, 99% of the time, full of worry about my life choices. This is an exhausting and deeply useless personality flaw. 

One of the things that I’ve found most helpful in combating this is hearing others matter-of-factly acknowledge the things they do to work their best. So. Here goes. An incomplete list of things that I’ve been deeply ashamed of:

• Ending sentences with prepositions.
• Being too pedantic. 
• Wasting time outlining.
• Shitty first drafts.
• Getting enough sleep. 
• Taking a walk when it’s light out. 
• Working out before work. 
• Pausing to talk to a friend. Or make a friend.
• Working on the weekend. 
• Working after dinner. 
• Billing too much.
• Overservicing clients.
• Doing billable work instead of my own writing.
• Ordering from a meal prep service to eat healthy.
• Having a monthly cleaning service. 
• Billing hourly clients for research.
• Taking the time to plan. 
• Saying yes to work that was beneath me, clients I didn’t click with, or projects I knew wouldn’t succeed.

Now, here’s another incomplete list of things of which I have been deeply ashamed:

• Not ending sentences with prepositions.
• Not being pedantic enough. 
• Not outlining.
• Not writing first drafts.
• Not getting enough sleep. 
• Not getting outside to take a walk when it’s light out. 
• Not working out before work. 
• Not pausing to talk to a friend. Or make a friend. 
• Not working on the weekend. Not working after dinner. 
• Not billing enough. 
• Underservicing clients.
• Doing my own writing instead of billable work. 
• Not eating healthily enough.
• Wasting time cleaning.
• Not billing hourly clients for research.
• Not taking the time to plan. 
• Saying no to work that was beneath me, clients I didn’t click with, or projects I knew wouldn’t succeed.

You see the trap, of course. There’s always guilt.  

I think it’s partly because I know exactly how fortunate I am to be doing what I love. I know what it’s like to be on your feet every shift. I know what it’s like to be doing inventory at 4 am. I know what it’s like to close your eyes at night and see the conveyor belt on the backs of your eyelids. I know what it’s like for overtime and dysfunction and sexual harassment to be the norm. 

But this also means that I have paid my fucking dues. 

Here is what is true. 

I am a sought-after professional writer with more than twenty years of experience in one of the most complicated, highly regulated industries on the planet. I can parse a clinical trial or a poster presentation in my sleep. I can media train an executive. I can create a press release and a scenario plan and an annual strategy. I can tell you how to get people to care about your company and I can tell you why they don’t. 

I sit with biopharma executives who make more than a year than I’ve made in my lifetime and draw out their most interesting, eloquent, forward-thinking, thought-provoking selves. It’s my job to convince the world that they are brilliant. (Which, let’s be clear, they are. I am not a creator of masquerade, and I do not work with people who do not impress me.) 

I am very good at what I do, and that is where I’m best. 

It is so hard for me to say this that there are tears in my eyes as I type this, but here’s the truth. I am worth the money that I’m paid, and to be as good as I need to be at my job, I have to set myself up for success without shame. 

This may seem extraordinarily obvious to you, dear reader, in which case I envy and admire you. I’m putting it here in part because I think perhaps there are other people who struggle like me. But most of all I’m putting it here because I need to get it down and out for myself. Thank you for witnessing it.