The Plunge

October 10, 2013

I've written here and here about my love of money jobs that support freelancing or a growing small business. Since 2005 I've supported my freelancing with serving and bartending at seven restaurants, a couple of nannying gigs, and an interim position as a middle school drama director. Before Ben started working for himself full time (at the beginning of 2011), he worked at a restaurant as well. I've loved working in restaurants because I've met awesome people, observed lots of different humans, and learned more about food. I like shaking a mean cocktail, and I adore talking about the perks of truffle oil-- it's worked out well.

But it's been my for dream for 2 years to transition to working for myself full-time. I've continued to wait for THE PERFECT TIME, half expecting a gigantic thunder clap from the universe when the move was deemed safe. I didn't get a gigantic thunder clap, though. Instead I got a feeling in my gut, which is much more ambiguous than a thunder clap. It was persistent. I asked myself a lot of questions before I trusted my gut (and checked our bank account and incoming invoices, naturally):

#1- What do I expect this change to look like? What will I be doing with those 10-15 extra hours? I got really specific, a la Kathleen.

#2- What do I need to do to make it successful? I know I need to make sure that I see/work with other humans on a regular basis, because I get a lot of creative energy that way. I also know that I need to avoid trying to work all the time just because I can. I will burn out really quickly.

#3- Am I expecting this to fix challenges that I'm facing? If so, what challenges, and how? I have a really realistic (unglamorous) idea of what this will look like, and how hard it will be. I think this is healthy. I do know that working 35-40 hours a week will feel more manageable than trying to fit in 50-6o hours a week, especially once I start more rehearsals.

#4- Is missing that extra income going to add additional stress to my life? Only a healthy amount. I think it will force me to take some risks that I might not otherwise.

#5- Will I feel huge amounts of shame if I have to take another part-time job in 4 months? Absolutely not. I can only do my best, cheesy as it sounds.

I'm reminded of my interview with Emma Freeman, when she talks about deciding to take The Plunge into working for herself. She said that sometimes you just need to throw your whole self into something in order to know if it will work. That's exactly how I feel-- I've grown tired of dipping my toe into the pond.

In all honesty, something that's really helping me make this move is that I've had a hella intense 6 months of life. The beauty of dealing with lots of big, scary shit is that sometimes you feel more willing to take risks-- the fears start to feel less daunting. And today I'm grateful for that, and for the opportunity to try a new adventure.


  1. Best of luck to you as you take the plunge! How exciting!!

    1. Thanks Meghan! It's good scary (I think), but mostly exciting!



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