I caught that dream I was chasing. Now what?

Guest post by Sylvia Hook
I got this awesome squirrel… now what? (Photo courtesy of PrideBites Squirrel PrideBite Dog Toy)
I got this awesome squirrel… now what? (Photo courtesy of PrideBites Squirrel PrideBite Dog Toy)

Have you ever seen a dog chasing a squirrel? Have you seen the look of surprise and bewilderment on the dog’s face when it caught the squirrel it was chasing — almost by accident, it seems? Chasing a squirrel, or a dream, is fun. You’re not risking a lot, because it’s not like you’ll actually catch it, right? But then you do… and suddenly you have this squirrel in your mouth, and you don’t know what to do with it, except shake your head back and forth a bit and growl to assert that you really did it. You caught the shit out of that squirrel!

But now what? What do you do with this elusive concept of a squirrel, once you’ve finally caught it? Suddenly, it’s real — and maybe you’re no longer sure you want this squirrel. Maybe a different squirrel wouldn’t be quite so big and scary?

When I was 12, I began co-editing a newsletter with my mom. Although she suggested this as a more appropriate use for my copyediting tendencies than, say, correcting my friends’ emails, I wound up primarily handling the design and layout side of it, while she did most of the copyediting. And slowly, I fell in love. When I was 14, I decided I wanted to be a freelance graphic designer when I grew up.

Fast forward to 2011. My brother bought a farm (his dream), and asked me to help him with the visual identity — the first start-from-scratch visual identity project I ever did. He also encouraged me to start my own freelance graphic design business, helped me brainstorm names for my business, let me squat my website on his hosting plan, and offered to pay for my domain name. In short, he believed in me more than I believed in myself. Since then, he has referred clients to me, and continually encouraged me to follow this dream. Thanks to his help, I’ve more or less caught this squirrel dream.

But here’s the thing: it’s scary.

Between struggling with impostor syndrome and being afraid of my own success, it would be so much easier to curl up in a ball under the covers and wait for it all to go away, or at least get a steady paying job that doesn’t involve being a small-business owner.

Even beyond that, when you get up close to a squirrel dream, you find out that it has teeth and claws its own drawbacks — such as complicated taxes, and keeping track of hours, and generally various shitty paperwork that needs to be done by someone, and that someone is you.

So, when I’m feeling overwhelmed by this dream I’ve caught (which, to be fair, is more often than not at this point), it’s important that I take a step back and think about why I wanted to do this. And that “why” — because it lets me set my own hours, help other small local businesses, avoid “selling out” to a large corporation, and, most importantly, do what I love — is what keeps me going through the shitty paperwork. That, and remembering that I’d probably have shitty paperwork in any job, and at least most of this has a reason.

So go, chase your dreams, and if you catch them — growl a bit, shake your head back and forth, and then remind yourself why you were chasing them in the first place.

Comments on I caught that dream I was chasing. Now what?

  1. This is the most serendipitous OBHL post I’ve read in a looooong time. I, too caught my squirrel this year, and am nearly going crazy with anxiety, doubt, and fear over it. It’s nice to see that other people feel the same way after achieving great successes. Sometimes I feel guilty about my feelings since so many people are struggling to find basic jobs right now, and I managed to get exactly what I wanted, so what “right” do I have to feel this way? Thanks for sharing your experience.

    • Yay! Congrats on catching that squirrel!

      One of the best parts, for me, of being part of the OBH&L community has been realizing that there are other people out there struggling with the same things I’m struggling with. The two posts I linked to in my post (on Impostor Syndrome, and Fear of Success) were like that for me — they articulated things I was feeling, and made me feel less alone. And that’s a big part of why I wrote this post.

      • Hi Sylvia! I’m so glad to hear my article (fear of success) helped you to articulate your own thoughts! I’m glad you then wrote your own article to help out even MOAR people! YAY for the helping train! I love knowing I’m not being alone in my crazy thoughts :D.

        I really understand this feeling you’re having here. Although I haven’t quite caught my squirrel, I know that once I do…it’s going to be weird. I’ve been working so hard for this goal and yes, what if it’s not everything I envisioned? You have a great attitude about it: remember why you love it and just get through all the lame stuff that comes along with it.

        Some people don’t get to do something they really love for a living, so I just try and be grateful and do my paperwork 😀 Thanks for writing this!

  2. “I’m trying to find my squirrel”
    “I’m trying to catch my squirrel”
    “Horray! I’ve caught my squirrel!”

    Too bad I will probably get confused looks saying this to the general populous 🙂

  3. Thank you. Just thank you. I am in the exact same situation right now as a designer and I struggle everyday with ALL OF THIS! I tell myself it’s just me being down on myself, but it means the world to hear your story and know I am not alone. Thank you!

    • You’re welcome! Knowing that there were almost certainly others (and plenty of them) going through the same thing was a huge part of why I wrote this — so thanks for commenting! 🙂

  4. I caught my “squirrel” this year, too. Now I’m just wondering what comes next. If I’ve achieved the goal I was working towards professionally (and I’m young), what goal do I set next to keep me motivated?

  5. Thank you for the reminder that everyone has concerns about following a dream. I am up to my armpits in shitty paper work for my own business and it sucks, but it is mine( f*ing tax season). I have also worried about whether this squirrel was worth catching.
    I worked as a commercial glass artist for someone else for almost 6 years and last summer I quit working there and started working for myself, thank goodness my husband brings home a steady pay check.
    How long is it going to take to figure out all the ins and outs of being an artist and will there ever be enough money coming in? I have no idea but I have this fuzzy little guy in my grip and I am not letting go, can you hear the growl?

  6. When you catch your dream, you gotta set a NEW dream, and that dream is “make enough money to pay someone else to do the shitty paperwork.”

    I’m still working on that phase.

    • Get an intern!! There is definitely someone who would love to learn how to do what you do on a daily basis and you can even offer school credit if you go that route. That way you don’t have to pay for it but the paperwork gets done by someone else… and you get to help someone looking to learn about your business and career. Win!

      • Be careful. In the United States, unpaid internships in which the intern does more or less the work of an employee are actually illegal under federal labor laws. I don’t know anything about internship laws in other countries.

        Non-profits and government organizations can have unpaid volunteers, but for-profit businesses are legally required to pay anyone who is doing work that benefits the company at least minimum wage.

        Internships that are primarily for the education of the intern like job-shadowing setups or company run classes in which the company isn’t getting any immediate benefit out of the arraignment can be unpaid.

        Unpaid probationary periods are also illegal.

        Here’s a good flowchart of this information. It is directed at interns, but it works for people hiring interns, too:

        And here’s a fact sheet from the US Department of Labor: http://www.dol.gov/whd/regs/compliance/whdfs71.htm

  7. Thank you for writing this!! I currently have said squirrel in my mouth and am standing there wide-eyed and dumbfounded, wondering what to do with it. Do I bite down and finish the job, or let that sucker go?? You just gave me the motivation I needed 🙂

  8. I’m still chasing my squirrel, but every time it gets a little closer I have to stop myself from running into a shrub or otherwise sabotaging my own attempts. This was helpful to remind me that while catching my dream may be scary and hard, it will be worth it.

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