Alone, Together

Our team members share the joys and challenges of working for yourself. 

Week of the Website is built on a contractor-centric model. Our team members work with us because of the caliber of clientele, the freedom to flex their creative muscles, and the organizational support. But they also work with WOTW for all of those reasons that people are drawn to working as a sole contractor: freedom, flexibility, variety and more.

On our podcast, No Surprises, our producer Reyna turned us on to her Jewish summer sleepaway camp ritual - roses & thorns. So we decided to have members of the WOTW team share their favorite parts — and biggest challenges — of being their own boss.

Alex Lucke, developer

Best: Flexible schedule for sure — it allows my life to feel fuller.
Worst: Torn between feeling like I should always be doing more and loneliness.

Mallory Ulaszek, co-founder

Best: Flexibility in schedule.
Worst: Never being able to fully disconnect — but in reality, I love what I do, so that’s OK!

Justin Mabee, developer

Best: Working whenever you want.
Worst: Always feeling like you’re behind or not doing enough.

Jeannine Gallagher, project manager

Best: Flexible schedule and being able to make your own system/structure/process and create the environment/vibe you want.
Worst: The slippery workaholic slope.

Claire Harper, project manager

Best: Having the ultimate creative say in what you produce.
Worst: Not having other people to bounce ideas off of — unless you're really intentional about creating that kind of support and community.

Anna Potter-Malone, project manager

Best: Having clientele who understand that you are the end all/be all and there is no ‘speak to the manager’ vibe.
Worst: The difficulty of working around other schedules in the household.

Susan Lee, developer

Best: Freedom! Self-development. Not having to deal with a toxic workplace.
Worst: Doubt with every move you make and loneliness if you have people in your life with traditional jobs.

Samantha Gong, administrative assistant

Best: Flexible scheduling! When I'm feeling meh I can always step away and do something else without judgment or someone hovering and asking what I'm doing.
Worst: Sometimes it feels like you're not doing enough, especially when your day ‘ends’ early.

Molly Each, content editor

Best: Making your own schedule, being able to nimble when it comes to kid-related curveballs.

Worst: The inability to turn off while also feeling like you can never catch up.