Originally published on 1 October 2025, back when Freelance Forward was running on Brevo. Updated and republished for our growing community.
Hey Freelance Friends!
The gig economy is no longer a side‑hustle niche, it underpins a growing share of work. Platforms like Upwork and Fiverr connect millions of independent professionals to clients worldwide. Yet, as investors chase the next big AI story, they often overlook a more fundamental opportunity: Upwork’s structural advantages make it both a strategic investment and a more sustainable home for freelancers.
A recent AInvest article argues that Upwork’s lower fees, protective mechanisms and access to high‑value clients mean freelancers can build predictable income streams while investors tap into a resilient business model.
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Upwork’s cost structure preserves a larger share of earnings and reduces friction in long‑term collaborations. Fiverr’s higher commissions and delayed payouts discourage freelancers from pursuing scalable, recurring contracts.
Learning from Laura Briggs – building scalable freelance income
Freelance coach Laura Briggs used Upwork to transform a modest side hustle into a thriving business. She began earning about $1 200 per month, then landed a $50 000 ghostwriting project by digging past low‑pay listings.
Her strategy included:
Targeted search and personalized pitching: Briggs ignored entry‑level gigs and used keywords like “SEO” and “legal” to locate clients who valued expertise. Only 15 % of freelancers customize their pitches, yet her tailored proposals helped her earn more than 90 % of income from retainers.
Focusing on retainers: By converting one‑off assignments into recurring contracts such as email newsletters and SEO blogs, she built predictable revenue and worked with clients who view writing as a strategic investment rather than a cost center.
Leveraging platform visibility: An active Upwork profile with strong client feedback continues to act as a digital résumé, attracting new clients even as her business scales.
Briggs’ experience underscores how a deliberate search strategy, retainer‑oriented services and an optimized profile can turn Upwork into a sustainable career platform.
Market performance and investor insight
Upwork’s business fundamentals align with macro trends. Its tools foster deeper client relationships and reduce churn, while the Upwork Enterprise division targets large businesses, a high‑margin segment. Despite market volatility, a five‑year comparison shows Upwork’s stock outperforming Fiverr’s, highlighting resilience.
Investors benefit from:
Undervalued metrics: Current valuations do not fully price in Upwork’s lower fee structure and premium client access.
Gig‑economy tailwinds: Remote work adoption and small‑ and medium‑enterprise (SME) demand for flexible talent fuel long‑term growth.
These dynamics suggest that both freelancers and investors can capitalize on Upwork’s positioning as the freelance economy matures.
Strategic advice for freelancers
Prioritize retainer‑friendly services: Offer recurring deliverables like monthly content writing, social‑media management or website maintenance. Upwork’s escrow and milestone features simplify long‑term contracts.
Invest time in keyword search and custom proposals: Using specific terms and tailoring pitches dramatically increases your chance of landing high‑value clients.
Maintain a polished Upwork profile: Positive reviews and a clear portfolio act as an ongoing marketing tool.
Plan cash flow: Although Upwork’s fees are lower, always budget for the 10 % service charge and ensure funds are available during escrow periods.
The AInvest analysis frames Upwork not just as another marketplace, but as a strategic asset for both freelancers and investors. Lower fees, robust payment protection and project‑management tools mean freelancers can build stable, retainer‑based businesses.
Investors, meanwhile, gain exposure to a platform capturing the secular shift toward remote and freelance work while trading at attractive valuations.
Whether you’re a freelancer seeking sustainable income or an investor looking for undervalued growth, Upwork’s potential is too strong to ignore.
— Your Freelance Forward Fam ✌🏼
Tool of the week
Bonsai
Streamlined admin: Bonsai was designed to handle the tedious tasks freelancers don’t want to deal with so they can focus on paid work. It rolls proposals, contracts, time‑tracking, invoicing, expenses and even basic accounting into a single dashboard.
Seamless workflow: You can create a proposal, convert it into a contract, and auto‑generate invoices, all within the same platform.
The built‑in legal templates save you lawyer fees and ensure your agreements are solid.
Retainer‑friendly features: Bonsai supports recurring payments and auto‑follow‑ups for unpaid invoices, making it perfect for freelancers who want predictable income through ongoing contracts.
Time tracking + invoicing: Its integrated time tracker lets you log hours with one click and instantly convert those hours into invoices. Ideal for Upwork freelancers who want to manage off‑platform clients in a similar way to Upwork’s milestone/time‑tracking system.
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PROFREELANCE (Pty) Ltd
2023/279056/07
The content in this newsletter is for informational purposes only and does not constitute financial, legal, or professional advice. Pro Freelance and Freelance Forward are not affiliated with or endorsed by the platforms or tools mentioned (unless stated otherwise), and we are not liable for any losses, damages, or issues arising from your use of them. Always do your own research before making decisions related to your freelance business.
