From Elance to Upwork: What 17 Years of Part-Time Freelancing Really Looks Like

Built on the Side: Real freelance stories

Derrinita Walker began freelancing during the recession, when Upwork was still Elance. Seventeen years later, she has worked across presentation design, branding and fiction writing while keeping a full-time career—and has learned why a sustainable side hustle is sometimes about protecting time rather than chasing the biggest possible income.

Freelancing Started as a Recession Safety Net

Derrinita earned a design degree in 2007, entering what was then a crowded and popular career field. She secured a paid internship with a state agency and later moved to a private construction firm.

Then the US recession reached the construction industry. As work slowed, her three-person team was reduced to two. The company retained the more senior employees and reassigned her responsibilities.

A small severance helped temporarily, but she still needed income while looking for another job. Freelancing offered a way to use the design skills she already had without waiting for the perfect permanent role.

She joined Elance—the marketplace that would later become part of Upwork—and concentrated on the work she knew best: PowerPoint presentations.

“Freelancing was a way to use my skills and keep myself afloat until I could secure something more permanent.”

Her First Clients Bought Low-Cost Presentation Design

Without reviews or a platform history, Derrinita competed largely on price. She discounted her services heavily and targeted presentation projects where she could show relevant experience.

The low rates helped win early work, but her approach was not only “be the cheapest.” She tried to understand what each client wanted to achieve and showed that she cared about the outcome rather than simply producing a file.

Over time, the work expanded into light logo design and writing. Derrinita says the common thread was asking enough questions to understand the client’s real goal before starting.

That willingness to investigate became one of her strongest advantages. On a freelance platform, where proposals can feel interchangeable, a specific response to the client’s situation can demonstrate more value than a long list of software skills.

A Romance-Writing Job Changed Her Direction

Derrinita’s biggest shift came when she applied for a short-romance writing project. She had loved writing since childhood, but until then graphic design had been her primary freelance identity.

A positive review led to more creative work. For several years she wrote flash fiction, novellas, detailed plot outlines and complete role-playing game scripts. Editors helped her develop her voice, and the variety made the period especially rewarding.

The change also created a problem she only recognised later. Moving freely between presentation design, logos and fiction was creatively satisfying, but it made her profile appear unfocused to some serious buyers.

“It was a lot of fun getting to bounce around different kinds of design and then leaving design entirely for writing. But it made for a disjointed profile.”

If she started again, Derrinita would choose a clearer niche and build a more coherent body of work around it. Breadth can help someone discover what they enjoy, but it can also make prospective clients work harder to understand what they are hiring.

Top-Rated Status Gave Her Permission to Raise Her Price

Not every contract went smoothly, so achieving Upwork’s Top Rated status felt significant. It gave Derrinita evidence that her wider record was strong and encouraged her to move her rates closer to the level of experience she had gained.

She now sets her freelance hourly rate around 20% above the equivalent rate in her day job and increases it by two or three dollars every few years. Because she has full-time employment, she can be selective and prioritise projects she expects to enjoy.

That is a different model from someone trying to maximise platform revenue. The side hustle must justify time that would otherwise belong to evenings, weekends, errands, exercise and relationships.

The Honest Numbers Behind a Long Freelance Career

Derrinita reports approximately $12,000 in cumulative gross freelance revenue. That total spans work dating back to 2009 and should not be read as annual income, profit or a steady monthly wage.

A typical recent month produces roughly $175 gross, while her best month reached about $1,200 gross. She estimates net income at around $85 in a normal month, although the exact amount varies depending on platform fees, software costs and when fixed-price contracts are released.

Her income can fluctuate sharply. Hourly clients may reduce or postpone allocated hours, while a fixed-price contract can create a large payment in one month for work completed over several months. In quieter periods, Derrinita says revenue may only cover her subscriptions.

Her current Adobe and Canva subscriptions cost approximately $1,080 a year. That means the economics of a small creative side hustle depend heavily on pricing and utilisation: professional software can consume a large share of revenue when client work is light.

This is precisely why Derrinita’s story is useful. It shows the version of freelancing that sits between “failed experiment” and “six-figure business”: a flexible, long-running income stream that has delivered meaningful work and extra money, but not consistently high profit.

A $200 Fixed-Price Project Exposed a Costly Pricing Mistake

Derrinita describes pricing as one of the hardest parts of freelancing. A recent fixed-price contract paid $200, but she estimates the same work would have cost approximately $1,100 if billed at her hourly rate.

The gap came from committing before the scope was sufficiently clear. She has since become more deliberate about asking questions during the initial conversation, especially when a client proposes a fixed fee.

A fixed price is not inherently worse than hourly billing. It becomes dangerous when the deliverables, revisions, source material or approval process remain vague. The freelancer then absorbs the cost of every hidden complication.

Her experience points to a simple protection: translate the expected workload into hours internally, add room for revisions and uncertainty, and confirm what is excluded before agreeing the final amount.

She Rebuilt Her Schedule After Running on Five Hours of Sleep

Derrinita used to accept almost every customer. She would finish her day job and then fill most evenings with freelance commitments, sometimes sleeping no more than five hours a night.

That schedule was not sustainable. Now, on freelance days, she leaves work at 5 pm, handles errands or goes to the gym, eats dinner and returns to her home computer around 8 pm. She tries to limit client work to three weekdays and, when necessary, one weekend day.

The boundary reduces potential earnings, but it also makes the work more durable. Derrinita is candid that having no children does not make her time unlimited: household responsibilities, health, friendships and rest still compete with a second job.

Her Best Proposal Tactic Came From Job-Interview Advice

Derrinita changed her proposals after seeing a video about answering “Tell me about yourself” in a job interview. She adapted a three-part structure associated with Dorie Clark: briefly explain the past, describe the present and then state why this particular opportunity makes sense.

That final element matters. By applying selectively, Derrinita can write an authentic reason for wanting the job instead of sending the same generic proposal repeatedly.

By contrast, she considers paid proposal boosting one of her least effective tactics. She spent additional Connects trying to place proposals at the top of the list, but says it did not materially improve her results. Applying early and demonstrating direct experience proved more valuable.

“I was able to differentiate myself when I applied early enough and could show my direct experience with jobs like theirs.”

AI Has Changed the Creative Work She Once Loved

Derrinita says the fiction sectors where she found much of her work now rely more heavily on AI-generated content. The shift reduced opportunities in an area that had given her years of creative satisfaction.

She occasionally uses AI to create placeholder or concept content when a design client has no budget for finished copy, but she is uncomfortable using it as a substitute for paid creative work.

That tension reflects a wider change in creative freelancing. AI may speed up early-stage ideation, but it can also reduce the market for entry-level writing and encourage clients to treat specialist work as an inexpensive add-on.

Derrinita’s response is to lean more heavily into communication, consultation and judgment—the parts of the work that depend on understanding the client rather than simply producing more assets.

Seven Lessons From Derrinita’s Journey

1. A side hustle can be useful without replacing a salary. Derrinita’s freelance work provided a safety net, creative opportunities and extra income across different stages of her career.
2. Discounting may win the first job, but it needs an exit plan. Early low-cost work helped her build reviews; Top Rated status helped her justify gradual increases.
3. A clear niche reduces buyer confusion. Variety was enjoyable, but a disjointed profile made it harder for some clients to understand her strongest offer.
4. Fixed-price work still needs an hourly calculation. A $200 project can become an expensive mistake when the real workload would justify $1,100.
5. Paid visibility is not automatically worthwhile. Derrinita found that proposal boosting mattered less than applying early with directly relevant experience.
6. Software costs can erase small-month profits. Recurring subscriptions should be measured against realistic revenue, not the best month.
7. A sustainable calendar is part of the business model. Protecting sleep, health and relationships may be more valuable than accepting every available contract.

What Comes Next

Derrinita is considering a weekly LinkedIn article series to demonstrate her design and communication expertise. She hopes the content can direct suitable prospects to her Upwork consultancy and support her tutoring work on Wyzant.

It is a logical next step. After years of relying mainly on platform search and invitations, publishing useful ideas under her own name could give potential clients another way to assess how she thinks.

Her advice to new freelancers is concise: be patient, because getting noticed can take weeks, and be clear in profiles, proposals and terms of service. Vagueness wastes time for both sides.

The Bottom Line

Derrinita’s story challenges the assumption that every successful side hustle must become a full-time business. Her reported revenue is modest compared with the exceptional earnings stories that dominate social media, but the work has survived a recession, a platform merger, several creative pivots and the arrival of generative AI.

She has used freelancing as a safety net, a creative outlet and a selective source of additional income while maintaining a primary career. She has also experienced the less photogenic parts: thin months, expensive software, underpriced projects, lost sleep and crowded marketplaces.

That makes the central lesson unusually credible. Longevity comes not from accepting everything, but from clearer positioning, better questions, gradual price increases and the willingness to protect a life outside the work.