10 Lessons Learned Spending $100,000 on Upwork

I stumbled around for a couple years - making loads of mistakes.

I wish I had a cheat sheet on lessons learned, so I put one together.

Here are 10 things about hiring remote via Upwork I wish I knew sooner (#7 was most painful)
1. Tasks expand to fill the time allotted to them. If you give an upworker (who you are paying hourly) 10 hours to write one sentence, they’ll find a way to bill you for the 10 hours. Be unreasonably time restrictive.
2. Time zones can be a struggle. If there is any communication needed on your project, be sure to note it in the ad. If you don’t do this, you’ll be up at 9pm trying to zoom with someone you are paying less than $10 an hour. Not high leverage time.
3. How They Do Anything is How They Do Everything - I’ve literally seen posts that say “I have a superb attention to deetail”. If they mispell in their profile, how will they do with your work? If they can’t join a zoom with good video and audio, how are they going to write code?
4. If you don’t have time to document a good process, or meet with your upworker routinely, then you shouldn’t hire one. Ambiguity is the death of a remote worker. Be Clear in your instructions!(See point 5)
5. The lead research guys are machines. “Hey I need the name info and home address of left landed CEOs in Manhattan by tomorrow”. POOF - spreadsheet in your inbox when you wake up for like twenty bucks.
6. Make sure anyone in the Philippines has two sources of the internet, and sends you a copy of their internet speed test. Typhoons can be a kick in the ass, and really mess with your mojo.
7. Freelancers can be mercenaries. I had one who worked for me for a year, and the day we let him go, contacted all our competitors trying to sell our database. This was an American. We caught him, but that’s a story for a different thread…
8. Conversely, I had an incredible woman who started as an assistant for me on upwork, and now is a key executive in one of our companies. She is a true friend, and is incredibly competent! Talent can be anywhere. Five years and still going…
9. For longer term roles, we pull the contractors off upwork after a period of time. I want upwork to make plenty of money from the connection, but once the role goes long term, they need to be off the platform.
10. Use the hell out of the “Five Paragraph Order” . This simple format is a game changer:


If you want me to send you my template and overview of the Five Para Order throw me a quick follow then slide into my DMs
Bonus #11: Keep good reviews and write good reviews. Better people will work with you if you have a five start profile. I’m proud of the positive feedback I get - even if it’s from a small project.

What would you add to the list?
@SamtLeslie As requested. @SullyBusiness What am I missing?

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