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42 contributions to Six-Figure Freelancers
🚩 Red Flag Bingo
Every one of you has a client you should have run from. You saw it. You felt it in your gut. And you took the job anyway, because rent is a real thing that exists. Here's the one time I actually listened. Guy reaches out on Upwork. Real name, real photo, real-looking company behind him. Good gig, too. Then, pretty early on: "Let's move this off Upwork — no sense in both of us paying their fees." Which, fine. Normal people float that. But something was off and I could not have told you what. So I looked him up on LinkedIn. Profile was right there. Same name. Same face. Still felt wrong. So I messaged that guy on LinkedIn and asked if he was hiring writers on Upwork. 👉 He said that isn't me. Somebody had taken a real person's name and photo and was out there hiring freelancers with it. The flag was never the off-platform ask. The flag was the feeling I almost talked myself out of. So let's play a game. Here's the board. 👇 🚩 "This should be a quick one." 🚩 "We're looking for a long-term partner." (On a $150 one-off.) 🚩 "Send over a few ideas and then we'll talk budget." 🚩 "Our last writer kind of just... disappeared." (So did the two before her.) 🚩 "What's your best price?" — asked before anyone has mentioned scope 🚩 "It's basically done. We just need someone to polish it." 🚩 "We're like a family here." 🚩 "This probably won't pay much, but the exposure is great." 🚩 "Just a few small tweaks." — round nine 🚩 "I'm not very technical." — proceeds to rewrite all of your copy 🚩 "Can you hop on a quick call?" — ninety minutes, no agenda, three people who said nothing 🚩 "My budget is flexible for the right person." — the budget is $200 🚩 "We need this Monday." — sends you the brand guidelines Friday at 6:47pm 🚩 "Our CEO wants to weigh in." — CEO has not read it, will not read it, will have notes Alright. 👉 How many did you get? Drop your number. Now... ❓ WHAT DID I MISS? Every one of you has one I didn't put on there. The specific line. The exact words that made the hair on your arms stand up — and that you ignored anyway.
2 likes • 7d
All of the above! Story: My late husband and I met with a prospective client that was a nonprofit organization. We’d work with other nonprofits in the past with no problem. So we met with this group. Typically we would meet for an hour with a potential client to find out what they needed, to get to know them, let them get to know us, and then usually close the deal. This day, when we met with the organizations top executives, they were constantly interrupted, running off to do something, answering questions from staff, and never really had a coherent conversation with us in over 2 hours! What a waste of time! So a few days later when they called and said they were ready to start, I told them we were already booked and suggested they go somewhere else. My husband was shocked that I turned them away! I told him it was obvious that they would be a “black hole“ client, meaning that we’d spend hours and hours and hours, and because they were never clear on what they wanted, we would never get compensated for our time invested (because we billed by project, not by the hour). That was the first time I actually turned down a potential client – and what a sense of freedom that was!
1 like • 7d
@Nick Bandy 🤣🤣🤣
Cold email won by a landslide
Not close, either. 15 votes for COLD OUTREACH. Organic inbound took 8. Ads and warm network got 2 apiece. So that's where we're going. Now — I said in that poll that I compare job boards to Tinder, and I want to finish that thought, because it explains this whole thing. On Upwork, somebody posted a job. They have a budget. They have a deadline. They have already decided they're hiring somebody. The only question left is WHO. That's Tinder. Everyone in the building is there for the same reason. You still have to not be weird about it, but the hand is already up. Cold outreach is the grocery store. Same you. Completely different odds. And the difference has nothing to do with how good you are at your job. Here's the good news though, and it's bigger than it sounds. You don't need a new system for this. 🎯 TARGETS. 💣 PAYLOAD. ⏰ TIMING. Same three dials. They don't care whether there's a job post involved. But two of them get harder — and one of them stops being a dial and becomes the entire machine. 🎯 TARGETS gets harder, because nobody filtered the list for you. On Upwork you can pull up a client's history and decide in thirty seconds. Cold, there is no history page. You're building the list yourself, which means you can aim literally anywhere. Which is exactly why most people aim at "businesses in my city" and then wonder why nothing lands. 💣 PAYLOAD gets harder, because there's no job description to respond to. On Upwork, they TOLD you what they want. Cold, you're guessing. Evidence still beats proxies. But now your evidence has to be about THEM — not about the job they posted, because they didn't post one. ⏰ And TIMING? TIMING becomes everything. Think about what a job post actually is for a second. It's a timestamp. It is somebody standing up and announcing "I need this NOW." That is the single most valuable piece of information in the entire transaction — and on Upwork they hand it to you for free, a few hundred times a day, with a budget attached.
Cold email won by a landslide
1 like • 18d
I have two: My best client probably hired me right after they realized another quarter had slipped by and their big goal still hadn't moved. My best client probably hired me right after they grew enough to get busy, but not enough to have a boss or partner holding them to anything. I have been an accountability coach for others for almost 6 years - working for a company who let me go last year. So I’m thinking of starting my own accountability coaching service. Granted it’s trading hours for dollars. But it will give me the income sooner than anything else I’ve tried. (I’ll also check Upwork for similar job postings.) So cold outreach with these issues is an approach to consider!
⏱️ 2-Second Poll: Where do you want to aim next?
SIXers... Everything I’ve shown you so far—TARGETS, PAYLOAD, TIMING—I learned from starting on Upwork. But the three dials don’t care where you use them. These matter for the cold outreach I'm doing right now, too. They matter when I reach out to potential affiliate partners. They matter whenever you are communicating with anyone, to accomplish anything. Upwork is kinda like a "lukewarm, halfway in between cold and hot" outreach. It's why I always compare job boards to Tinder. But... Taking shots, looking for evidence instead of proxies, and keeping a floor work anywhere you’re trying to turn a stranger into a deal. So where should we aim next? Please vote below, and if you're feeling really extra credit, do us a BIG favor and say which SPECIFIC type of outreach channel you're interested in.
Poll
27 members have voted
1 like • Sep 29
I say cold outreach because I am so brand new in building my list. I only have three people! But hey, I’ve got three people! So anything I can learn on how to do cold outreach – whether it’s emails, LinkedIn articles, Facebook post, whatever is valuable to me!
⏰ TIMING: Good months are traps
Feast and famine! Sucks, doesn't it? Here's a recap of what we've seen so far… 🎯 TARGETS. Who you aim at. 💣 PAYLOAD. What you drop on them. ⏰ TIMING. When you show up. We're on TIMING today, and it's the third dial that secretly screws up the other two. I'll go first, because I ran into this for years. I told you in the TARGETS post that I was sending five proposals a week when I felt like it, or twenty-five when I panicked about money. I framed that as a volume problem. It wasn't, really. It was a rhythm problem. Five and twenty-five weren't two different habits. They were the same habit, measured at two different points in a cycle I couldn't see. Good month → stop. Bad month → panic. Repeat until you conclude you're bad at business. And here's the part I want to be fair about. Stopping made sense. I had work. Projects with dates on them. Clients who'd actually paid me. And prospecting was the only thing on my list with no deadline attached, so prospecting was the thing that could slide. Nobody emails you to ask where this week's outreach is. (Unless I'm coaching you 😂) So you drop it. You did the responsible thing with the hours you had, which was fulfill the projects you got already. That's what makes this so hard to spot. It doesn't feel like a mistake while you're making it. It feels like focus. Eric said: Longer clients make him feel more secure in his income, so he doesn't push as hard. Which eventually backfires. It just depends how long before the backfire lands, and whether a straggler client delays the panic. "Relief from influx of money." That was his phrase and it's exactly right. And it runs in the other direction too. Israel said he stops when he gets discouraged, not when he gets comfortable. Pascal said he's been the guy who doesn't fire for three months because nothing feels good enough to shoot at yet. Different doors leading to the same room. 👉 Full, so you stop. Crushed, so you stop. Either way your pipeline is running on how you feel, and how you feel is a terrible operator.
⏰ TIMING: Good months are traps
0 likes • Sep 19
The memes are particularly powerful! 😆
2 likes • Sep 19
@Nick Bandy Yes! Whew! Thank you!
Heads they buy, tails you die
Ryan Serhant does multiple billions of dollars in real estate sales every year. His secret? "The Two Cs." That gets your foot in the door. But is that his real secret for closing deals? Watch this quick short and drop a comment what you think his real "secret" is for closing billions in deals.
1 like • Sep 15
Relationships. Mark’s back to the old saying of people buy from people they know, like and trust. Be that person they know, like and trust!
2 likes • Sep 15
@Nick Bandy Listening instead of talking. Asking questions instead of volunteering information. I’m still learning how to do that with email. 😆
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Kip Piper
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24 points to level up
@kip-piper-6003
Serial Entrepreneur since 1991!

Active 5d ago
Joined Dec 1, 2025
Las Vegas, NV
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