Whose job do you really want?

A different approach to career progression

At some point in almost every job I’ve had, my manager asks me to ‘look around and think about whose job I want’ in an attempt to chart my career progression. Every time I’ve been asked this, I’ve looked around and thought I don’t want any of these people’s jobs.

Did I want to be Head of Research? No. Did I want to be Head of Product? No. Did I want to be CEO? Definitely not. 

I used to think it was because I wasn’t particularly ambitious. I didn’t care about career progression, I just wanted to do a job I enjoyed that paid well.

Eventually, I realised it wasn’t a lack of ambition that made this question hard to answer, it was because I genuinely didn’t want any of those people’s jobs. Yes, they were better paid, had higher status and more decision-making power, but from where I was sitting their day-to-day didn’t look that fun. Their calendars were often filled with back-to-back meetings, their role having morphed into management and away from their original craft.

I wasn’t inspired by the career ladder in front of me, but I didn’t want to stay stagnant either. I needed a new challenge. So instead I went self-employed.

In an attempt to understand this new world of self-employment, I immersed myself in the work of other creative freelancers. I started reading their newsletters, attending their workshops and setting up coffee meetings to chat. I quickly realised there were so many more ways to make a living than I had ever imagined.

It drastically shifted my perspective on where I could take my career. What used to feel like a narrow linear concrete path now felt like a sprawling forest with paths in all directions. 

One stand-out workshop I attended was an introduction to quilting. The workshop was run in a beautiful studio with massive sash windows that let gallons of natural light into the space. The walls were covered in colourful wall hangings and shelves of beautiful fabrics. As soon as I walked in I was in awe. 

image credit: Made My Wardrobe

In the centre of the room was a woman who seemed so totally relaxed, so at ease, so calm. I soon discovered her name was Lydia and she runs Made My Wardrobe.

For the next 3 hours alongside learning to quilt, I quizzed this mythical, magical woman about her career. I wanted to know everything. What led her to set the business up, what was she doing before, does she employ people, which arms of the business make her the most money, which parts does she do and which parts does she outsource?

I learned what started as a challenge for her to make her whole wardrobe from scratch transformed into a business combining in-person sewing workshops, one-off commissions and designing sewing patterns so others could make their wardrobes too.

I couldn’t believe this was her job. It seemed so dreamy spending all day creating or bringing others together to create. I walked away from the workshop thinking I would love to have this woman’s job.

The workshop prompted me to revisit the usually dreaded ‘whose job do you want’, question but this time allow myself to look much wider than before. To careers that seemed totally out of reach. To people who had drastically different backgrounds to my own. 

And I was surprised how easily other people came to mind.

The next was Maisie Hill.

Maisie is an author, podcaster and coach whose work explores both the menstrual cycle and cultivating more power in your life. She has written 3 books: Period Power, Perimenopause Power and Powerful. She also runs an online programme which combines coaching and teaching on all of the above.

I feel so drawn by Maisie’s overall vibe, the way she conducts herself with such calm confidence. I love the topics her work explores, being interested in both women’s health and the power of mindset. And I love how she brings women together to help them better understand themselves.

The second person who came to mind was Emma Gannon. I’m an avid reader of her newsletter

The Hyphen by Emma Gannon

and love hearing about Emma’s life as a writer. The idea of making a good living from a newsletter sounds so dreamy to me. She’s published both nonfiction and fiction books and interviewed hundreds of fascinating people on her podcast Control Alt Delete. She’s also a coach and hosts creative unblocking workshops in beautiful locations. 

I love the flexibility of her lifestyle which allows her to work from lovely cafes, go for swims in the day and to move to New York for a month.

Lydia Higginson, Emma Gannon, Maisie Hill

So those are 3 people’s jobs I actually want: Lydia from Made My Wardrobe, Maisie Hill and Emma Gannon. Not one of them is a user researcher or even works remotely closely to product design. Which at first felt unsettling. Have I ended up in completely the wrong career? Which career should I pick? Sewing? Writing? Coaching? 

But on further inspection, I uncovered some common threads that connect them all. 

Firstly, creativity. All 3 of these women have highly creative careers. For Lydia it was sewing, for Maisie and Emma writing, podcasting and designing coaching programmes.

Secondly, community and connection. The bringing together of people either in the physical or online space. The community of The Hyphen newsletter, the group coaching of Maisie Hill and the group sewing workshops of Lydia. 

Finally, freedom they are all self-employed or small business owners. None of them have massive multi-million dollar global companies. None of them have a staff of hundreds working below them.

Pulling out these themes allowed me to see parallels between what I do and what these people do. 

For me, freedom is my recent transition into self-employment. Creativity is in designing research studies, crafting creative reports and hosting ideation workshops. Connection is through interviewing participants from all walks of life, having coffee dates with other freelancers and writing this newsletter.

But it also draws attention to where my work is falling short.

I’d love to dial up both the creativity and connection elements in my work. I’m not totally sure what that might look like. Maybe I’ll dip my toe back into design, perhaps I’ll put more time into my writing, maybe I’ll put my coach training to good use and design my own group coaching programme. I’m sure it will take time to figure out but having an awareness of what’s important and what’s lacking allows me to better dream up futures that feel fulfilling.

So whose job do you actually want? Look further afield than the narrow hierarchy in your company or industry. Look to people in completely different industries, with totally different backgrounds to you. You might end up with a seemingly random, unconnected list, but the gold is in finding the threads that connect them all.