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Five years ago, I left a 15-year career in advertising to work for myself in an entirely new field. Recently, I solicited questions about this for people who are considering the same. This post is part of a series where I'll be answering some of those questions. In many cases, I've combined questions that were similar.


How do you take that first step? What do you need to take into account?


I don't think there's one all-encompassing first step, so I'm going to lay out three that I think are most important when you're considering a big leap.

1. Drop your practical voice and allow yourself to dream big. Then, don't let that dream go.

Yes, practicality matters. Money is real. Responsibilities are real. Most people cannot just up and quit what they're doing today to do what they wish they could do. I certainly couldn't. But so often, we think these kinds of things boil down to practical measures. As in, if we can't logically see it, it won't happen. But what we can project plan our way into is so limited; there are so many more possibilities than our minds can see. As David Whyte said, "What you can plan is too small for you to live" and I know this to be true. A good plan is great, but it's just a tiny part of it. We can't possibly imagine the depth of what is available for us.

My idea of becoming an author at 37 was so stupidly illogical. I had six figure debt, I was a single mom, I had invested tons of money and time into my career: a graduate degree, trainings, and all those years of experience. I knew nobody in publishing and had no idea what it took to publish a book. My cost of living was expensive, I was exhausted all the time, and I just could not see how it would possibly, practically happen.

But. I held this vision. I clung so tightly to the belief that it would happen, somehow. And I spent time really envisioning it. I imagined what it would feel like to work from home (or anywhere I wanted), what it would be like to create my own schedule, have wide-open creative time, and do things like go to the beach in the middle of the day (or whatever) just because I felt like it. I felt this in my body. I mocked up book covers with my name on it (and a New York Times bestseller designation). I made vision boards. I clung and clung and clung to this dream and I did not let it go.

I read books like The Big Leap, The Great Work of Your Life, The Art of Possibility and more. I infused my brain and heart with thoughts of possibility constantly.

The people I know who have made big transitions like this expect it to work out. They expect to be surprised and wowed by life, even in the face of rejection and negativity.

2. Start doing what you hope to do now.

Alongside all that dreaming, I also took action.

I started writing weekly blog posts and producing a weekly podcast years before I finally left my job. I didn't make any money doing these things and a lot of it was crap, but I did it, and I kept doing it. I produced work. I tried out what it would be like to be a writer, a creator, a producer, and a marketer of my own work. I built a website. I started promoting on social media. I woke up early to write and wrote in between work meetings (and sometimes during them). I was newly sober, so I tapped out of almost all social stuff and worked on creating these things instead.

This accomplished two things.

First, it allowed me to see what it was really like to do the work I wanted to do, because sometimes we have a fantasy of what something will be like, but once we start doing it, we realize we actually hate it or at least don't love it enough to put all the effort in that it takes.

Second, it helped me build connections in this new space. I started to connect to other writers, coaches, teachers, podcasters. As a podcast host, I got to meet so many incredible people by interviewing them - people who would later blurb my book, invite me onto their podcasts, etc. I started to build a community on social media and an email list, so that when I finally did quit and was ready to sell something, there was an interested audience.

It might sound depressing to think of waiting months or years before you make the big leap, but for me, doing this work was so exciting, joyful, and fulfilling. It made my job-job seem less important and also less awful, because I knew I was working towards something else. And each little step really does matter. It's actually the only way to build anything. The first time I submitted a piece to be published on Elephant Journal and I received approval from them, I squealed in the train station! It was a big deal. The process is the whole gift.

When the time finally came to leave my job I had a couple of years of real experience, a little bit of confidence that I could make it, and a decent network of connections.

An important thing to note is, I didn't think about all of this work strategically. It didn't even feel like work. I went where my energy and interest and curiosity flowed. I did it because I couldn't not do it, and I think that's how you know you really want it. It doesn't have to take years. There's no magical timeline. But you should absolutely start doing what you want before you leap.

3. Put people in your life who dream big and make big moves.

This may be the most important piece of all. If everyone in your life is comfortable with the status quo, it's really hard to get momentum. You won't have the kinds of conversations that are energizing and helpful, the people you're talking to will be annoyed, bewildered, or disinterested about your ambitions, and it's just incredibly hard to move forward.

Meeting new people requires effort, yes, but it's totally possible. Reach out to people who are doing work you love (and are reachable - don't go for the #1 bestselling author or the absolute leader in the field - try for people who are building around or slightly above your same level). Make a wish list of people you'd love to connect with. Ask people to coffee. You don't have to limit it to people in your desired field, it's also great to talk to people who have made other moves, people who live boldly, who are fascinating risk-takers and seem to have what you want. Rising tides really do raise ships.

Note: Do NOT ask people if you can "pick their brain". Don't ever use that phrase at all, actually. :)

On the flip side, don't talk about your dreams to people who can't understand or are invested in you staying the same. It will only deflate you. These dreams are so important and they need to be protected. Choose who you share with wisely.

I'll be answering more questions in the coming weeks about the specifics of my own leap, including what my circumstances were, practical matters like savings and health insurance, what my biggest blocks were, and more.

Tell me what you think below!

Photo by Thiago Thadeu on Unsplash

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