Reader Question: Jamie

Q. Dear Jordan,

My question is, how do you juggle it all? I have always wanted to be a writer/artist/fashion icon/actress/several other things. I have always played it safe though, opting for jobs with benefits and 401ks…etc. Currently, I am the Office Manager for a Physical Therapy clinic who spends her days verifying insurance claims and daydreaming. How were you able to put aside your fears of failure and just “go for it”?

Reading your blog inspires me daily. I just wanted you to know that your daily “adventures” motivate me to push myself harder toward what I want to become. Thank you for being such a motivation to me, and, I am sure, to many other readers as well.

Keep enjoying life to the fullest and telling us all about it!!

Thank you,


A. Hi there Jamie,

Before I get started answering your question, thank you! Your email means so, so much.

First, it’s important to address the very real risk factors at play when you choose an “unconventional” career path. It’s not just “fear of the unknown” – I know exactly what I’m scared of: not having enough money to pay the gas bill or buy groceries, let alone have a baby one day. When it comes down to it, in some ways it really is a question of resources: do you have the resources to devote yourself to your passions…or can you create a situation in which this might be possible (for example, working a day job and writing at night)? In my case, I was very fortunate to have my husband’s help: I worked at an insurance-having-type job for nearly two years while Kendrick toured with Harlem Shakes, and when the band broke up he decided to do the same for me, so I could jump in head-first. That’s not to say I wouldn’t have figured out a way to do it if I didn’t have his help; just that I don’t discount how fortunate I am in this regard.

I know that sounds scary, but the truth is that it’s a scary path to take. There are billions of ups and downs – one day, you get a book deal or a TV show, the next it’s gone – and the most important thing is to approach it all with some element of Zen. Confidence. Belief in yourself. (I also should probably try taking my own advice to heart.)

Logistically, balancing all these different careers can be difficult. You have to be able to prioritize (handing in that freelance article edit is probably more important than responding to a reader’s query about where to have dinner, even if the reader response is more fun to write), be unbelievably organized (I track each and every single thing that I have to do in my iPhone calendar), and work as if someone’s watching over your shoulder every second…even if that someone’s just your cat (I’m up every single day around 8:30 and on my computer by 9, no matter what…weekends included).

If your blog has two readers, you have to write like you’re writing for a million. If the only person wearing the clothing you design is your best friend, put as much into that dress as you would if Cate Blanchett was about to wear it on the red carpet. Don’t slow down just because of setbacks, or because things aren’t progressing exactly as you’d like. You’ve already reached your goal: doing what you love to do every single day.

Like I said to reader E., test the waters. Go on a cattle call audition (just tell your boss you have a doctor’s appointment), write a spec article for a blogger you love, buy some watercolors and spend a Saturday morning painting away. Living the life you dream of isn’t a feat of magic, and you don’t have to be superhuman to do it – you just have to be very, very clear about what it is that you love, and determined to transform “what you love” into “what you do.”

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