Freelance Marketers Stuck Feeding Upwork to Survive
Experienced freelance marketers consistently struggle with acquiring and retaining clients, often relying on platforms like Upwork. This difficulty prevents them from scaling their businesses into agencies and leads to financial instability and burnout, highlighting a core challenge in independent marketing careers.
SOURCES (60)
“… is one of the biggest lessons I’ve learned in business. We had a pretty successful Product Hunt launch which drove a ton of traffic to our website, as well at our first 70+ paying users. It was an overwhelming feeling as a founder refreshing…”
“Took on a client who sells will writing services. I created an on-brand landing page that looks clean, modern and good on mobile. He insisted I use his landing page, fine. I started with max conversions right off the bat on Wednesday got 7 leads, next day, double the budget was spent, same number of leads. Over the weekend, got no leads. Currently at £900 spent with 19 conversions, and he messaged me saying that it's quiet and they've got nothing in. I regretted not starting with manual”
“read a founder's story where he said pricing is a filter for your clients. he started at $500. 11 leads, 9 said yes but half argued about scope, and 2 ghosted the invoice. constant hassling, energy and time wasted. moved to $1,500. cleaner, but still got the "can you also just quickly" requests. moved to $3,000. 9 leads, 6 closed, average time to close: 2 days instead of 9. zero scope fights. one client even said "good, i was worried you'd be cheap." he kille”
“When I first decided I wanted to consult creators, I thought I had a simple job. Study YouTube. Learn storytelling. Understand hooks, retention, packaging, audience psychology... Eventually I'd know enough that people would naturally want my help. That wasn't what happened. I still haven't made much progress getting clients. For a while, that made me think I just didn't know enough. So I studied even more. More videos. More breakdowns. More frameworks. Then I realized something.”
“This is what every successful consultant learns sooner or later. Some work is too expensive--for you, not the client. I'd even cut out the "get the best possible version" stuff. Just go with 'We build the product that gets you funding.' The key to pipeline is building relationships. For this specialty, you'll want to get involved with local startup groups, investor groups, and VCs. You don't know what actually gets funded, so learn more about that. It's your sec”
“3 clients before the site is honestly the best validation. build the boring bits later lol, nice win”
“If you fill a need or solve a problem, you can find clients. That slow-and-steady growth will serve you well, especially in the beginning. Make sure you ask your clients for testimonials and recommendations -- that will be a key section on your own website (which you really should take a weekend or so and get even a basic one up and running).”
“Your instinct is right tbh. the clients who lead with "how cheap can you do it" are always the worst clients, they nickel and dime you through the whole project, scope creep everything, and leave bad reviews anyway. losing them isnt a loss, its a filter. The only thing id watch is making sure your premium positioning is backed by proof. "we build the best version of your product" is a claim, and serious founders will want to see case studies,testimonials, or at least a portfo”
“Hi, i have been running a marketing agency for 1 year now, no clients, i don't know what to do, i ran ads for myself, cold called, cold email, nothing, only 2 clients who i worked for, for free, got good results but they don't want to do their part of the work which i did for them at first for a case study but i still didn't get. I don't know what to do anymore, i tried so many offers, paid, free, free trials, no one wants to work, i know i can get good results or otherwise i wou”
Took me about 6 months of focused content publishing to land my first real consulting client. The hardest part I didn't anticipate was how much time Id spend on prospecting calls that…
“I'm a digital marketer with an educational background in Design and Journalism and 4 years of industry experience. The first two years, I was working full-time as a Social Media Specialist for an in-house department at a Pest Control Company until I was laid off. For the past two years, I've been working pro bono as a Content Writer & Strategist at a non-profit journalism outlet while paying the bills with a part-time caregiving job. My portfolio covers all of my work from those four”
“I used to believe the lie we’re all sold “ Just do excellent work and people will notice. ” For years I was that guy. Best numbers on the team. Fixed problems no one else could. Delivered consistently. I genuinely thought my work would speak for itself. It didn’t. The promotions and opportunities kept going to people who were good enough but extremely good at making sure the right people knew what they were doing. Meanwhile, my work was getting absorbed into “ team effort ” or credited to my man”
“Spent a few months chasing HIPAA and TCPA compliant builds for med spas, insurance agencies, real estate teams, HVAC companies. Landed zero of them. My first paying client had nothing to do with any of that. He came from my friend's mom's friend, someone who heard through a chain of people that I build stuff, and he wanted a video made for a kids' show called Jungle Jam. Not the compliance-heavy, impressive sounding build I'd spent months chasing. Just a video for kids. Closed hi”
“I’ve come to learn that if you’re in a group that services M&A it’s just as rough. They give the most ridiculous 1 day turnarounds and it screws you up. I wish someone had told me this. submitted by /u/Throwaway1920214 [link] [comments]”
“I've had my business for four years now, a social media and virtual assistant company. It SO depends on the client and how receptive they are to what you say, even how you present it to the. You do need to prove your experience (I've had some clients where this was a must) and I get that. Some need hand-holding as well - social media and admin are totally uncharted waters for some people. Completely understand how that sets a precedent. My advice would be to first define your guns, then”
“This is very simple, yet also the hardest thing to do. Simply detail the challenges that you are facing and that you want to deliver a high-quality service, but feel that you unfortunately don't have the information you need to do so. Don't blame her or tell her anything is her fault, but you can list off the things that you need in order to be able to complete the work. End it by just telling her that, at this time, you regret to inform her that you won't be able to continue to supp”
I lost more deals to my own spreadsheet than to prospects saying no. Three tabs, a CSV of 400 companies, sticky notes for who I'd already called, and a shared list where…
“Similar path here, running about 12 decks a week for clients now with a two-person team, down from 20+ hours of manual work to maybe 6 since we layered in a few tools including Oria for the slide drafting side. The reselling angle you mentioned is where things actually compound though, because now you're not just billing for delivery, you're building recurring access on top of a system someone else already proved out”
“How did you start an agency? I worked for two, I'd like to know how you even get started. I'd imagine you need a lot of capital to start with.”
“Hi everyone, I've spent nearly a decade running a small company specializing in mindful branding, helping founders translate their vision into visual identity and market positioning. Throughout this journey, I've noticed a common problem that kills startup brands before they even get off the ground. It's the struggle between two extreme branding mindsets: 1. The Trend-Follower (The Chameleon Trap) These startups are so obsessed with market demand and "what's trending" t”
“On the referral fee mechanics: a flat one-month fee tends to work better than a percentage, because it's simple to explain and doesn't make the referrer feel like they're haggling over your client's lifetime value. The bigger unlock though is who you ask. Client referrals dry up partly because happy clients don't think about you between problems. Referral partners, other professionals who serve your client type but don't do what you do, refer continuously because they'”
“Mine was from my network too. That first trust gap is the hardest part so warm leads close way faster.”
“Biggest fail is selling cheap social media work before you know how to get results for one niche. Get clients yourself first and learn sales and retention before hiring anyone. If you want local leads fast then SocLeads can help you build outreach lists from Google Maps and socials but dont build a team till you can keep clients for a few months.”
“Urgency is always a tell. It can either be your best leverage or your exact downfall. Your discernment and ability to go slower in consideration will give you clarity in these situations, every time. I always scan for coherence and congruence, there's acceptable degrees to this... as well as tolerable and intolerable ones. It's a tell to the level of risk management you'll have to take on, afterall and what kind of equity you'd have after. You're right about not discounting y”
“I prefer to believe in the product or at least the people around me. But I'm also reminded of Winston Zeddemore's quote from Ghostbusters: "If there's a steady paycheck in it, I'll believe anything you say." Sometimes you stick it out because you're getting paid and getting benefits. But you should always be looking for the next gig, if you're doing it just for the money.”
“I relate to this. For me, the biggest trap is optimizing the business before validating the business. It's easy to spend hours improving: dashboards websites automations SOPs branding internal processes All of those have value, but they don't matter much if you're avoiding the work that creates revenue. The uncomfortable work is usually the work that moves the business: talking to customers following up on leads asking why someone didn't buy making offers collecting honest feedba”
“Just keep pushing... Have your preferred agent/model design a Complete marketing and business plan... have the plan include 14, 30, 45, 60, 75, 90 day milestones ... and be realistic when you collaborate with AI on the plan... keep AI grounded and realistic from the start... don't accept typical AI pie in the sky attitude but ground him in realism .. not negativity but more like goals that are actually attainable...”
“That's a smart way to grow. Solving one client's problem and turning it into something repeatable is a great example of building beyond one-off services.”
“They dictate how many days a week you'll come (they're home while you're doing this work), all the tasks you'll do but the scope keeps creeping and what time you'll do them in, how much they'll pay you, on what schedule etc etc... I just ended a client relationship before it started due to that behavior. 17 animals including 10 give or take outside cats who each get their own bowl of wet and dry food and have it washed, dried and put away at every meal, vacuuming floors/f”
“I'm going through this crazy intensive training right now on building sales funnels and I'm actually getting pretty good at this 😃 But I need to practice on real businesses - not just fake ones. So I'm looking for 2-3 people who'd let me build the first page of their funnel for FREE. Want more leads? I'll build you a lead funnel. You want to sell something? I'll build you a sales funnel. You want people to book calls with you? I'll create an application funnel. No ca”
“I see where you’re coming from. Reads a little bit like my train of thoughts spelled out. Did you ever run into issues regarding limits? I’m currently on no paid plan because my previous promo deal for perplexity run out. So I got the drugs for free and now I question whether I get hooked or not.”
“CMO here, I'll go first. We were making content across X, Reddit, Instagram, and YT, and had a lot of trouble defining what worked vs what didn't. At this point, we knew nothing. Content was produced, engagement happened, got signups, but we had no idea what caused it. I made a system that solved this problem. 1. Content designed with purpose: Before any content is posted, it is put into a table describing which metrics the post is supposed to move. For example, this post is designed to”
“Yeah, I’m learning that one the hard way lol. What was the biggest shift that helped you turn attention into actual revenue?”
“I think when your business sucks your entire life, you need to stop and rethink for a bit”
“The gist of it is this: I have a potential client that I know I’m super close to closing but he is just squeezing my fee on and on. On the one hand it s a huge deal because of bigger credentials. On the other hand, he just won’t stop squeezing my fees. I’m a bit nervous because I feel it’s so close but on the other hand I feel like they’re playing me. What do I do? years ago I started a small Property management company. It has grown to a bit bigger now from residential properties - where I buil”
“Hey, I want to share a problem that I've noticed is very common among freelancers in my two years of experience: following up with clients and getting testimonials. Over the last two years, I've worked hard to make my clients come back. After finishing a project, I always check in to see if they need anything else. I work just as hard to keep my existing clients as I do to find new ones! However, I needed a system that could help me manage my follow-ups and get testimonials for each clie”
“I had a 1-on-1 consult with a social media fitness influencer offering online personal training last week and toward the end of the consult after asking me all sorts of questions, she told me the price about 5 months for ~£2400 ($3200USD). I had no idea what to expect going into the call or how much it is. She was asking how much do you have to set aside. I was telling her I was a student, and sorry it probably wouldn’t work out. I don’t make enough on top of expenses to sustain that and she pro”
“i undercharged for way too long because i was scared nobody would pay more. classic mistake. my saas was like 5 bucks a month. cheap felt safe. but cheap pulled in the worst customers, people who churned over any tiny bug, flooded support, and treated a 5 dollar tool like it owed them their whole life. i thought low price meant more customers. it actually meant the wrong customers. i finally bumped it to 19, hands shaking, fully expecting signups to die. they didnt. i got fewer tire-kickers and”
“for real, lean into the oddly satisfying stuff, that’s what people actually stop scrolling for wild how the “eh why not” posts end up carrying the whole business”
“We record every sales call (Gong, nothing fancy). For like a year I never once went back and watched an old one unless there was a deal on fire. Then one week I was stuck for LinkedIn content and re-listened to a demo from a few months back just to kill time on a train. The prospect spent four minutes explaining why their current tool's reporting was basically useless for their finance team. Word for word, that objection would've made a better hook than anything I'd written that quar”
“HELP!: Hi all. The terms above get floated so much around for transactional practices. I really want to build that as I’m having a slow start and am asked repeatedly to demonstrate the above. I get particularly anxious making judgement calls and require reassurance from seniors before sending off emails etc. is that normal? Can someone provide practical tips to overcome this hurdle? I want to improve. submitted by /u/bigmoviesperson [link] [comments]”
“Works for a self-taught freelancer with no degree/logos. A prospect's real fear is "what if I pay and they can't deliver" — a trust gap, not an info gap. So shrink the risk instead of arguing it away: offer a small, well-defined, paid test task before any big commitment. Paid (not free) attracts real hires; it flips the dynamic (they get evidence instead of your pitch); it de-risks both sides; and a large share convert to the bigger job. Scope it tightly, price it as a no-brain”
“I am a dummy, I don't do that....fortunately I have only been burned 1x....for a small amount”
“I worked at Google Ads for 2.5 years and started my own agency last year and I understood why most of the home services Ads account aren't getting good ROAS. Here's what happened - Initial situation: A small plumbing business was spending about $1K/month on Google Ads and wanted proof it could work before putting in more. The problem wasn't the budget, it was friction. Initial outcome: Their setup was search ads pointing to a landing page with a long contact form. In one month that p”
“I think -- once you've been turned down twenty times -- you'll have your head screwed on straight to prepare yourself for the results of advertising. Plenty have felt everything was ready before market reality hit them. Why is it, I wonder, you aren't using this time to develop socials, YouTube channel, and other low and no cost marketing?”
“Hoenstly I have had a fair few small to medium business clients get turned off on how expensive agents can get. So even if its business users are still on the fence”
“most networking is about building relationships before asking for referrals. local business groups, cpa events and casual conversations often work better than cold outreach.”
“I agree with you, and I think part of it is that digital marketing lets you feel busy without risking your ego. My first SaaS failed in a pretty boring way because I kept improving the product instead of forcing awkward prospect conversations early. Since then I try to treat every sales call as research with a possible invoice attached, not as a performance I have to win. It makes rejection less dramatic and the product gets better faster.”
“In total, we spent about 18 months cycling through agencies for our DTC brand. Each had an excellent pitch, a group of employees and an account manager who was never the one carrying out the actual work. The communication was slow, the results were insufficient and it took weeks to change course when something wasn't working. changed to working with a company, where Andrés is the sole person in charge of strategy and implementation. No account manager layer, no handoffs, just a person direct”
“So I was with an agency for about 6 month. Wasn't great. I think the most fans I ever had was about 300 and they had about 4 accounts for marketing. For the last 3 months I've been doing it my self. I'm only posting on reddit. I offer a free trial. And I'm average about 10 to 15 subs a day. And I have a very low resubscribe rate but I do sell and average about 500 month. My question Is this the best I can expect. Are these average number or with better caption or picture etc I sh”
“I wouldn't say I'm "better" at marketing, considering I've only been at this for around 5 months, but I'm definitely marketing it right. I marketing my business as "premium" and easy to work with. Simple online booking, quality communication, and overall just giving the user an experience that feels high-end.”
“As a client, I pay good to the people I have hired but someone recently told me that the quality of work I'm getting isn't that 'great' and that I should expect more from a freelancer or I should hire someone else. If you're paying more than what average clients pay, what do you expect from the person? Is it just the quality of work or something else? submitted by /u/elliewhimsi [link] [comments]”
“I am no expert and I think it looks different for everyone but I did a couple of things: 1) I made a list of everyone I had worked with that was employed at a different company and sent all of them messages asking if they had time to catch up at some point. If that conversation went well I’d ask if they were hiring and take it from there. Feels a little bad soliciting referrals like that but it helped. 2) I looked up social hours/ community events for my field and started going to every one of t”
“This clicked for me when the “customer” became one actual person, not a segment. Even a rough picture of their painful daily workflow makes the idea way less abstract.”
“Just had a call with them and it all sounds great but I am skeptical. Looking for anyone that has worked with them or still does, did you like it? Why did you leave? Why are you still with them? Did you see a good ROI? submitted by /u/cfierce [link] [comments]”
“That's amazing! Congratulations. Just curious, how did you get your brand out there?”
“You spent a lot of time reflecting and landed on 'lack of creativity' as the culprit, but I'd push back a little on that diagnosis. The businesses you described might have just been built on thin margins where a creative edge was the only differentiator. There are plenty of non-sexy, process-driven models like invoicing automation or compliance checklists where being methodical and reliable beats flashy branding every time.”