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For everybody in my DMs asking 'how do I start on Upwork': watch this first, then come back. The first 30 days are the hardest and few people show them honestly. My first month in 2017 I sent 40 proposals and got 1 job, $60. Na so we start.

Oluwatobi Adeyemi@tobi_freelance

September 13, 2026

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Usman Afridi@usman_fiverr1 rep in Freelance Files
sir thanks, very helpful. kindly tell, first month you also took small jobs below your rate?
2 net votes
Oluwatobi Adeyemi@tobi_freelance#1 in Freelance Files
Yes Usman, the first month and a bit. Small jobs for reviews, then raise fast. But small jobs, not free jobs. Never free
2 net votes
Sujan Shrestha@sujan_ktm1 rep in Freelance Files
haha 40 proposals for 1 job, I feel seen. my first client paid me in 3 parts because my bank wanted 3 letters for one remittance 😅
2 net votes
Keron Baptiste@keron_tt1 rep in Freelance Files
Trinidad checking in. First month I got a $15 job fixing a WordPress plugin and the client left 5 stars and a tip. Still my favourite client ever
1 net votes
Matheus Barreto@matheus_wp#9 in Freelance Files
Sending this to my cousin who wants to start. The first 30 days part is very true, Upwork is like a game where level 1 is the hardest
3 net votes
José Gregorio Marcano@chamo_coder#4 in Freelance Files
chamo, my first month I had no way to withdraw to Venezuela, so the money stayed in the account 2 months like a hostage jajaja. but yes: start small, raise fast
1 net votes
JoJo Ramos@jojo_navyvet#5 in Freelance Files
Bravo Zulu on the patience, Tobi. Watching this tonight. Thinking about a small side gig myself, so the timing is good
0 net votes