What happens when your side-project can’t sustain you?
This post is a one-year later follow up to “What happens when your side-project suddenly needs to sustain you.”
After spending the last year visiting some of the best teams in tech, I’ve seen the incredible calibre of work that is possible when a group of passionate people come together on something. That is so exciting to me. All of my favourite parts of Ways We Work have been connecting with people, whether it’s through 1-on-1 interviews, random Skype calls with readers or talking with larger groups on our team visits. I’ve had unique insight into careers and teams all over North America and the world. I understand what makes work meaningful for different people and now I want to apply that into a role where I can have a real impact on a team.
I never had any expectations of where Ways We Work would take me. When I started the site, I was in my first job out of University and was simply looking for a way to learn from others so that I could be better in my own career. Two years of interviewing more than a hundred professionals all over the world, travelling to San Francisco and New York to produce pieces on teams like Facebook, Spotify, Medium and more — it’s still surreal in many ways.
When Ways We Work celebrated its first year, it had already started gaining some serious momentum. Interviews were read around the world, the site won a web design award and a reader had featured us on Product Hunt. I’d never been a part of anything like it. Matt and I had already started experimenting with ways to include teams on the site, and shortly after that the opportunity to visit Facebook came along. There was so much happening, I was in between jobs and felt a strong urge to try and pursue Ways We Work full-time. Had I not taken that chance there’s no way of knowing how things may have gone. I can confidently say we wouldn’t have been able to do the trips we’ve done, and I wouldn’t have had the same level of focus and time to dedicate to the site. That first trip to San Francisco opened a lot of doors for us early on, I felt I owed Ways We Work and myself the opportunity to grow, and both myself and the site have done that.
In the last year we’ve made two trips to San Francisco to write features on seven different teams, and we just got back from New York where we visited three more. We’ve reached over a hundred interviews with people from cities all over the world. We’ve explored countless ways to monetize the site, a sponsored video series that didn’t work out, branded content, weekly sponsorships, we flirted briefly with becoming a recruiting platform. This past summer we were even approached about a potential acquisition but the conversation stalled. It’s been a rollercoaster of a year full of excitement, happiness, frustration and confusion. I’ve been in conversations I’d never be a part of in any other role. I’ve met people I probably wouldn’t have met and been places I probably wouldn’t have gone — at least not this early in my career.
I’ve learned hard skills like how to produce content people want to read, how to sell sponsorships and work with partners. Also soft skills like being self-motivated, how to communicate effectively and how to be a great listener. I’ve also learned some things I never expected to learn, like how to have a panic attack in the shower and then get right on a call and sound confident despite how in over your head you feel. Bonus: I’ve learned the key skill of packing for a week in only a carry-on backpack. It’s been a year stuffed to the brim with experience and I’ve pushed myself to what I thought was my mental brink many times, only to learn I can go much farther. When it’s just you, you can’t stop because then everything stops. If you’re not sending emails, you’re not getting emails. If you’re not publishing content, you’re not getting readers and you’re not getting sponsors.
When I set out to do Ways We Work full-time last year, I had no five-year plan or expectations of where it might take me. So many times I’ve found myself in a tension between how I could make money through the site and the things I wanted to do with the site. By forcing it to be my sole source of income, I suffocated the love I had for it as a creative outlet. I’ve learned that it can be a business or a passion project and it can’t be both. My favourite moments working on Ways We Work are moments where I forget that it needs to financially sustain me, and make decisions based on what we want to do. The truth is, I don’t want it to be a business, I don’t want to stifle it anymore. I’ve been able to connect with people all over the world, both people I’ve interviewed and readers. But, a number on a screen telling you that thousands of people just read an interview, doesn’t replace working with real people everyday and thousands of readers doesn’t pay my bills. I don’t want it to have to. One of my favourite writers
, has been able to sum up my feelings on this completely:“The shadow side of doing what you love is that suddenly the thing you love now has to make money for you. And money plus love is not always a symbiotic relationship. For example, to turn a creative hobby into a capitalistic venture is to take away — at least in part — a purity of the experience of that hobby. There is a shift that happens when your passion no longer is a thing you do in your free time, but is a thing you do in order to allow yourself free time.” — from “What nobody will talk about when they say “do what you love”
I want to let Ways We Work be the passion project that filled me with so much excitement two years ago when I started it. I still plan on doing interviews and team features whenever we can, it’s just not going to be my full-time focus. I want to continue thinking about what’s best for the site but I’m going to start doing a lot more thinking about what’s best for me too.
I’ve missed the connection that comes from collaborating with co-workers and the fulfillment that comes from working with people. I’m excited to leverage everything I’ve learned through Ways We Work in a role where I can have a real impact on a team’s culture and solve challenging people problems.
So if you’re looking for someone with my combination of insight and skills, I’d love to talk to you. I’d be so grateful for any leads on roles where you think I might be a fit. I’m particularly interested in roles that involve working closely with people like team leadership, talent acquisition, HR or communications but extremely open to exploring undefined and other roles. I’m passionate about building and communicating team culture both internally and externally.
Here’s my email: amandah@wayswework.io
Special thanks to
for inspiring this post and being so open about his own job search on Twitter. Thank you to , and for feedback and edits.