Let's craft the blueprint for your dream job

Today's show is a working session for your future career

This is the first episode of a new year together. Happy New Year. I hope this year brings you new opportunities and more importantly, the confidence to seize them.

I'm not much of a resolutions person myself, but I like to use the start of the new year to get clear on a vision for the year to come. In that spirit, today, I'm bringing you an exercise to get clear on your own vision for 2024. I'm inviting you to craft what I call the dream job description. That's right, we're going to kick off the new year with a working session.

This dream job description doesn't have to encompass anything you actually do right now or even anything you know how to do. It's intended to help all of us let go of the constraints, the real ones, the ones we imagine, the constraints that we normally impose when we think about our own paths. And despite the name, it has immediate, practical applications. You can use it to evaluate what you're doing right now. If you're considering making a change, it'll help you figure out the direction in which to nudge your thinking, so stay tuned.

How this exercises helped during my own career crisis

Now, this is an exercise that I've done myself. Back in 2018, six years ago now. I was generally a very unhappy version of myself. It had been building for a while and I hit this point in my career where things really needed to change. Now, partly I was at the wrong company. It just wasn't a great fit. But mostly, I'll admit this, it was me. I'd gotten to what felt like the middle of my career and I'd hit the goals I had for myself. I was a respected writer. I covered technology, an industry I cared so much about. Along the way, I outgrew some version of myself. I just felt totally burnt out and I knew that I needed to look for another job, but when I would look at other jobs that I seemed qualified for, none of them seemed interesting to me.

At the time, I worked with a coach named Robin. She introduced me to this exercise, the one we're going to do today: formulation of a dream job description. When I first did it, I didn't believe in it at all. I gave her a really hard time about completing it, but I took a chance on it anyways because that's how unhappy I was. I just figured, I'm going to do whatever somebody else tells me to do. I found it transformative. Writing down things that I wanted allowed me to see that I wanted them in the first place. In truth, the things I wrote down felt too big to want, but when I just let go of the idea that they absolutely had to happen and focused on what they could be, my idea for what I wanted became bigger. Now, whenever anybody comes to me for advice, I always offer up this exercise for them, and I'm going to tell you, it works. I'm certain of so little in life, but I'm certain of this.

In March, 2018 when Robin asked me to write my job description, I told her that I knew the things that lit me up, but I didn't see any jobs out there that were going to let me do those things. I mean, I wanted an interesting, meaningful gig that didn't take up all of my time. I wanted time off to write a book, paid time off where I would keep my healthcare benefits because my wife had just found out she was pregnant. And by the way, I wanted a significant paid parental leave. I mean, when I wrote it down then, and even when I think about it now, I have to ask, isn't this just too much to want, too much to ask? Robin urged me to put my notions of what was possible to the side and to pretend my way to the perfect role for me, and I did. I sent her a draft...

...and she sent it back. She asked me to think even bigger.

What did my office look like in this new job? How much money did I make? Was I certain about that? What was I responsible for achieving? Why did it matter to me? The end result was a one-sheeter for a job that I really thought couldn't possibly exist. But I knew that I felt great about it. I knew it really would be the perfect job for me. I printed it out, I folded it up, I slipped it in my wallet. Today, I have a version of that job. Every last thing I described manifested in the job that I took a few months later, and if you'd asked me then, I would've told you that it all came out of the blue. But that's not really what I think, especially after hosting experts on careers for five years now on Hello Monday.

I've come to believe that we can only achieve what we can imagine, and often we limit our imaginations before we even know what we want.

As you've heard me say on this show, I've come to believe that we can only achieve what we can imagine, and often we limit our imaginations before we even know what we want. Drafting my dream job description broke me out of the limits and the constraints of how I thought about what I could do. Once I could dream it up, that job became much easier to find. I really hope it does the same thing for you.

Versions of this exercise abound. The designer, Debbie Millman, who's been on our show, she offers up one called a Ten-Year Life Plan. She took the idea from the designer, Milton Glaser, who had been assigning it to students in his class for decades. It also comes up in our Hello Monday episode with the Stanford professors, Bill Burnett and Dave Evans. They talk about designing our lives.

It's been almost six years now since I did this exercise myself. I read it and I realize it sounds kind of dated. My dreams have expanded, so as the year kicks off, it feels like a good time for me personally to do this exercise again, and I hope you'll join me.

The exercise: directions

Okay, here we go. I want you to take a moment now to gather your tools. You're going to grab a pencil and a paper, a pen, or if you'd prefer to do it on a laptop, that works too. That's how I do it. You're going to need a minimum of about 15 minutes for that first pass. This is an exercise that takes time really as much as you want to give it. Choose a quiet spot, a place you know the kids aren't going to bust in just when you're hitting your stride. I often pull my laptop into my lap on the sofa just under this large southern-facing window that gets great light.

What's important here is that you approach this exercise with a clear mind and that you allow that mind to wander, so put your phone or laptop on airplane mode, silence your notifications and make sure you can't access the internet because if you can, my guess is that you will. One more thing. If you don't have moments of discomfort or even what feels like boredom in the next 15 minutes or so, you aren't doing this exercise right.

Okay, at the top of the paper, write dream job description for January, 2029. Yeah, 2029, that's 5 years away, and as we've seen, 5 years is not actually a lot of time, but it's just enough that you can imagine a complete change. Everything really could be different. So first I want you to imagine who you are. Take notes here. It's all part of the job description. If you don't know the answers to the questions that I'm asking, that's fine. Just make something up. You can always go back and change it. Do you live alone or do you live with a partner? Do you have kids? Pets? Are you a city dweller? Do you live in a place where you can take a hike every day? What are you wearing? Get really specific here. These details are going to help you. And remember, as you're taking these notes here, not to write down the things you think might be likely to happen in five years, but to write down the things that you know your heart wants to happen. Just be there in the want.

Now, once you're holding this idea in your mind, this idea of who you are, give your job a title. Again, make it up. That's fine. My job title was Head of Technology and Humanity at an important media brand. It was not one I'd ever seen on a job description. I'll tell you that. Now, write down everything about this job. What's the work? How does it get done? What is its underlying purpose and why is that meaningful to you? Where do you do it? Do you go into an office? If so, how often? What does your workspace look like? What are the tools you use? Who do you talk to every day in your job? Who do you make sure not to have to talk to? And what's their opinion of you? How flexible is your schedule? Do you travel?

Now spend some time here on benefits and compensation. What do you get paid? How and when does it change? When do you get time off and how flexible is it? What benefits are even important to you? Do you want a four-day work week or is it more important to you to be able to leave in the middle of a day on Thursdays for two hours to coach field hockey for your daughter? What is the path to advancement here? Where is your potential for growth?

Once you've jotted down answers to all of these questions, drop that text into a document on your computer and do a word count. Now, my first draft back in 2018, it was 225 words, which seemed kind of long to me, but then Robin asked me to make it longer, and that's what I'm going to ask you to do too. Whatever your number is, I want you to double it, make that your goal. Tell me even more about your job, what it feels like to do it, where it happens, how it happens, why it's the job for you. Here, sometimes accountability can be a helpful tool. If you'd like a reader for your job description, send it to me in the body of an email. Our show's email address is hellomonday@linkedin.com. I promise you two things. One that I will not share it beyond the Hello Monday team. And two, that I will read every single email I receive and I'll send edits.

If you'd like a reader for your job description, send it to me in the body of an email.

Now, you need to give this the space that it needs to sink in. Put it down for a day or even up to a week. When you pick it up again, make any final edits and then read it out loud to yourself. If you can print it out and put it in a place where you can find it. I stuck mine in my wallet, kept it there for a really long time. Then your job is just really to forget about it, the work here is done. You'll see for yourself the impact of this exercise and it will become a filter for you as you make career-related decisions in the year to come.

☕ Office Hours: Giving voice to our ambitions

I hope you'll come to Hello Monday's office hours this week to share some of your own discoveries from this exercise. I will most certainly bring mine. We will meet as we always do on Wednesday afternoon at 3:00 PM eastern on the LinkedIn News page. You can find a link in our show notes or in our newsletter, or you can email the team at hellomonday@LinkedIn.com and we'll send it to you.

🎉 Happy New Year! Here's to our fifth year...

I wanted to take a moment here to tell you just what a pleasure it's been to be on this journey of curiosity with you. I don't know, maybe this is your first episode with us, or maybe you're newer to the show. But maybe like Vionna or Ryan, you stumbled upon us during the pandemic when coming together once a week to check in felt like the one thing we could all reliably do. Or maybe like Jason or Tenisha, you found this show when we first launched it nearly five years ago. Everything was new back then. I was a new parent. I recorded a lot of those early conversations after sleepless nights of bouncing a very colicky baby. And like the show, my son is five now, my daughter's two. She's talking a lot and one of her very first phrases this past year uttered like an aside, it was, "Be back." If she went into the other room, "Be back." If she went downstairs with her caregiver, "Be back."

That's a good refrain for us. We'll be back. Back with more conversations that'll help us prepare for how work is changing, more new thoughts about how we can rise to the challenges of this particular moment. More ways to lean in and support each other when it gets hard, and celebrate the good moments too. Happy New Year to you!