Hot take: Should you take the steady retainer or chase the big project?

I had to choose between a $1500 monthly retainer from a boring logistics company or a one-time $4500 website build with a local coffee chain here in Portland. I went with the retainer because it felt safer, but three months in I'm bored out of my mind. The coffee chain gig went to another freelancer and now I see their work all over town. Anyone else regret playing it safe like this?

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1 Comment

joseph4858m ago

Man I feel this so hard. That $1500 retainer from the logistics company sounds like a slow bleed on your soul. I saw a buddy take a similar deal with a boring accounting firm and he was tweaking the same homepage button colors for six months. The coffee chain work popping up all over town must sting every time you drive past. Sometimes the safe play just ends up being a different kind of expensive, you know?