Before I started working remotely about two years ago, I was a little ashamed of my wanderer status. Sure, everyone loves the quote “Not all who wander are lost,” but when I tell people that I’ve moved over 20 times in my life their response is usually an indeterminable noise followed by silence. I think most people believe that not all who wander are lost, but most of them are. That unspoken judgment may be in your head or someone else’s. Either way, it’s a powerful obstacle.
But most of us benefit from some wandering. When I was working at San Francisco Art Institute I lost track of the number of conversations I had with artists who were coming back to art after a lot of time and life experience. I think wandering usually happens after following someone else’s rules for a while. Most of us find that rule-following is a poor substitute for making a life.
Not all who wander are lost: How to change careers after 40
1. Questions to ask yourself
2. Create the life you want
3. Design your life
4. Do! Or do not. There is no try.
5. Writing as a career and trusting your gut
I believe that with a little wandering all of us, including you, have the tools and skills to find a life and career that makes sense for you. I did, and it took me until I was 41 years old. I’m sharing the tools I used to do it now, so you can try them too.
1. Questions to ask yourself
When I was 26 years old I wandered into an opportunity that changed my life. I wrote a blog about it, so you can see everything that experience taught me. One tool I learned from Jelly Helm, my mentor and the founder of W+K 12 (among other things), is especially effective for changing careers. Asking questions.
This exercise is really simple and you can do it anywhere. You can do it with the Notes app on your smartphone or in a Word doc but I find doing it with a pen and paper works better for me.
Ask yourself a hundred questions. Write them down without stopping.
Sometimes I stop to count because I think I have enough, but other than that, just ask yourself a hundred questions. You can start with a specific topic for inspiration, but don’t feel like you have to limit yourself. Ask questions about your life, whether it’s worrying about your partner or what you forgot that morning. Ask big questions about life and the universe. Ask specific questions about a problem you’re trying to solve or an assignment at work. Just ask yourself questions.
No one will be grading this
You will probably spend some time just staring at the paper. That’s normal, but it’s important to ask the full hundred questions. Get stupid with it. Be vulnerable. Don’t decide what you’ll do with them after you’re done, just write 100 questions.
This exercise is especially helpful for me when I’m feeling stuck or when things just aren’t working and I’m not sure why. Sometimes I answer the questions when I’m done, other times the question itself is an answer. Either way, writing out questions I want to ask myself is useful.
This exercise gives me a clear picture of my hopes, concerns, and priorities at that moment. It helps me step back and evaluate where I am and what I’m doing. It helps me pinpoint what’s not working. Sometimes you already know what’s not working, that’s why you’ll want to keep reading.
You may feel like you have to do something with all of your questions when you’re done, but you don’t. This exercise is just about asking questions and seeing what happens.
2. Create the life you want
In 2012 I was sitting in the doctor’s office waiting for an appointment with my doctor. It was our first appointment, and I felt stressed. My bus was late so I had to take a cab to get to the appointment on time. I thought I had to be early to fill out paperwork, but I’d misunderstood, and it was irritating to be sitting there when I’d rushed to be early.
As I sat there fidgeting and writing an email response in my head to a challenging coworker, I picked up an Oprah Magazine from the messy table next to me. That magazine held an article that is my next favorite tool for changing careers.
What is an Odyssey plan?
I read the Odyssey in high school and I knew what an odyssey was, but I hadn’t heard of Martha Beck or “Creating Your Life.” This article helped me reimagine my future and anchored my ideas in reality. This tool made my wildest dreams feel not only accessible but realistic.
The article basically detailed instructions for creating a series of vision boards. It makes sense that this tool is so effective, we believe in what we see and the more often we see something, the more that vision becomes a part of who we are. Maybe I should remember that the next time I look at Instagram?
I strongly recommend that you read the whole article because her directions make this task feel like a joyful adventure. But instead of using the magazine images and scissors she recommends, build your islands on your mobile phone. You’ll understand what I mean soon. I use the PhotoGrid app and it works so well I haven’t looked for anything else.
There’s nothing like the internet for infinite imagery. It often takes me a handful of searches to find an image that feels just right. The word she uses is delicious, so your number one priority is to find images that feel delicious.
When I did this exercise the first time I switched steps 1 (dream life) and 2 (present-day). It was hard to think big while I was feeling stuck. So I started with a grid that looked like my life at that moment. Once I saw what my current life looked like from a little bit of distance it was much easier to envision my ideal life.
You may already be using Pinterest for this. After all, people use Pinterest boards for wedding planning, so why not life planning? But for me, Pinterest is more about collecting inspiration than prioritizing a vision. The app I use limits how much I can add to my dream board. This helps me focus on my top 15 priorities and helps me leave out the nice, but non-essential images. It also keeps me from focusing on the wrong things.
Narrow your priorities
Did I dream of buying a basket chair for almost 30 years? Yes! Was that basket chair in my top 15 life priorities? Nope. This board isn’t about stuff. It’s not about what your life looks like. It’s about how you want your life to feel.
I also use this Create Your Life exercise to make my work better. I use it for art projects, presentations, event planning, and book covers. I’m a visual thinker, so seeing my ideas and what I make alongside work that inspires me gives me a better idea of where I want to set the bar. It helps me see how far I really have to go to get where I want to be.
Another handy thing about using an app is that you can make your vision boards a screensaver on your phone. That’s what I do, and every time I look at my phone I’m reminded of what matters most to me and what I’m reaching for.
3. Design your life
Deciding to change careers didn’t come out of nowhere for me. People constantly told me how good I was at my job. I was never bored and my days were full of interesting people that I truly cared about. But have I mentioned that I’m an introvert? And did you know that college admissions is mostly meeting with prospective students, talking on the phone, and giving campus tours? I used up everything I had to give other people what they needed every day, so I didn’t have a lot left to give to my friends, family, and other projects.
You probably know what it’s like to have that kind of problem. Good and bad seem to balance each other, but you can’t quite ignore the feeling that something has to change.
If you’re like me, you spend a lot of time talking these kinds of problems out with your friends. That’s how I found out about Designing Your Life, from my friend Brie. It’s a book that’s based on a course at Stanford. A note before you pick it up, you have to do the exercises. The whole book will feel just like well-meaning advice if you don’t test their theories with your actions.
Energy vs. engagement
This book is great in its entirety, but two exercises in the book had a big impact on me. The first is the Energy-Engagement Map Worksheet. In the first paragraph of this section, I explain my situation as though I’ve always understood that my first career was engaging but draining. I didn’t.
I thought that, because I love those conversations, they were energizing. I was wrong. With this worksheet, I tracked my tiny everyday tasks for a week and it helped me understand not only what I hated doing, I had a pretty good handle on that already, but what tasks gave me more energy. Before this worksheet, I knew that writing was something I love to do. But I didn’t understand that writing helps me feel less stressed, even when I’m writing for work.
The 5-year plan
The other Design Your Life tool that I found really helpful was the Five-Year Life Plan. This exercise gives you a structure for reimagining your life. The first time I did this exercise it took three rounds of three to get it right because I kept limiting what was possible to the life I was already living.
It’s tough to understand, to really understand, that our lives can be completely different from the way they are now and that can be a good thing. It makes sense. Change can be terrifying and no matter how wrong things sometimes feel, our bodies and minds evolved to get used to anything we throw at them. That can make it really tough to take any leap, even an imaginary one.
This exercise can help you understand different possibilities for what your life could be and it gets you to create a loose path to get there. It’s also really fun to do, and I redo this exercise once a year, usually around my birthday or New Year’s.
4. Do! Or do not. There is no try.
When I started high school I was really shy and didn’t have many friends. I came up with a plan, see picture from my diary below, to become a cheerleader.
At this moment in my life, I spent a lot of time watching MTV, swimming with my sister, or dancing to CDs with my parents while they drank margaritas. I’d never done gymnastics or jumps or anything else that cheerleading required.
This was the early days of the internet, before you could easily find the instructional videos that are online now. I checked out the Internet Archive, and I would have needed to wait until 1996 before there was even a chance to check out cheerleading swag online.
Instead, I talked to family and a friend in my PE class. I watched what our cheerleaders did and I made up a training routine on my own. I don’t remember most of it, but I do remember a lot of high kicks. I trained in my bedroom every night for a few months. I did my best during tryouts and watched videos that I made of myself with our camcorder in the backyard. And I made the junior varsity team!
I’ve approached pretty much every goal that way ever since. Do, then keep doing.
Figure things out, sure. Take a class if it makes sense, but don’t just learn. Do the thing you want to do. Just start. It doesn’t matter if you do it right the first time. Best practices aren’t the end-all-be-all. Perfection isn’t the goal most of the time. Do, then do again, until you’re getting somewhere.
The essential second step
Pretty much every article about inspiration or life changes has a “Do! Or Do not. There is no try.” section, so I’m going to add a second step. Do you remember that video from Sasquatch where one guy starts dancing and eventually the video becomes a mass of wild enthusiastic dancers?
It wasn’t the first dancer who made it a sensation, it was the second dancer, the person who added to what the first person was doing. So, focus on your second step. When I decided to pursue writing as a career my first step was reading a book to improve my writing, and my second step was writing. Do, then keep doing.
5. Writing as a career and trusting your gut
Once you’ve done all this work and self-reflection it may feel like most of your work is complete. But it’s just the beginning. After I went through all of these exercises I knew I wanted to be a writer.
Around that same time, I started to understand all the different things writing can be. I started with advertising copywriting. I’d had a good agency experience and my first career was in graphic design with Van Gogh Vodka, so I immediately got to work writing and designing an advertising copywriter portfolio based on what I already knew and what I did before.
While I worked, I read the books you should read and I asked some creative director friends for critique. I knew I was onto something, but I needed more time to focus. So I did a little more soul-searching and took a leap. I knew that I couldn’t live in San Francisco at the lower salary a career change would require, so I quit my job and moved back to Portland.
Then it was time to focus. There are so many ways to be a writer: technical writing, SEO writing, copywriting. The differences between all of these different writing careers seemed confusing and vague to me. So I did some writing gigs I found on Craigslist. I took a community college class to improve my editing. Then I found an advertising course online from an ad school with a great reputation, Brainco.
Pay attention to what gets in your way
I thought this was it. Even though advertising didn’t feel a hundred percent right, I was hanging on to it for a couple of reasons. I mention this because I think these are pretty typical roadblocks for anyone changing careers:
- I already understood the ad agency world and had worked alongside copywriters. It felt familiar and therefore, more achievable.
- Ad copywriters make more money than most other writers. It’s hard to take a big pay cut to do something you love, so I was trying to avoid it. Lower pay can make you feel like you’re less important or valuable. I was already insecure about the shift I was making to writing, so the idea of taking an even bigger pay cut than I’d anticipated was scary.
But when I started this class I noticed a familiar and uncomfortable feeling in my gut. As the class continued, I realized I was dreading every session. Just thinking about that ad class made me feel like I’d had too many cups of coffee, in the bad way. Then I remembered another time I felt this way. It was how I felt when I worked at Wieden+Kennedy. At 26 that buzz was motivating and exciting. At 40, it just felt like stress.
Changing careers after 40 made everything better
It took a little bit more time, but I kept experimenting, learning, and narrowing my focus to find the right fit. I love writing long-form copy so I did some research into content writing. SEO sounded exhausting and mysterious. The qualities of SEO that I found scary initially are why I love search engine optimization today. I’d never looked at Google Analytics, but I quickly understood how essential it is and now I can comfortably set up and troubleshoot a GA account. I’m writing as a career and I love it.
Sometimes as I work on my laptop I pause and look around the room, like a kid at play expecting to hear that it’s time to come inside. That’s how fun this work is for me. Not all who wander are lost. Some of us just need some time to find ourselves.