5 Ways To Turn Freelance Gigs Into A Reliable Career Path

The 2025 State of Gig Work Report by resume platform Zety finds increasingly difficult conditions for gig workers. 88% are taking on more work to combat inflation. 91% report being deactivated, penalized, or banned without explanation. Almost half (47%) lack health insurance and retirement plans, and almost a quarter (24%) can’t always cover basic living expenses.

You may be committed to gig work for the variety, flexibility and/or autonomy it provides. However, you don’t want to get so busy moving from gig-to-gig that you end up with a haphazard career that doesn’t provide stable earnings and opportunities for growth. Instead, take a proactive and strategic approach to selecting your projects and clients, so you turn freelance gigs into a reliable career path.

1. Target Ongoing Retainers To Cover Your Basic Living Expenses

It’s hard to remain strategic in your choices when you’re hustling to cover your food, housing and other necessities. From a financial perspective, building a cash reserve of six months or longer can help ensure you don’t settle for sub-optimal projects or clients. From a career perspective, targeting ongoing retainers that are substantive enough to cover your basic living expenses is a good way to remain strategic about what other projects and clients you take on.

Previous Clients And Full-Time Employers Are Top Prospects

Look at previous clients who are large enough that they may need ongoing work. Negotiate a retainer agreement, even if it means you discount your pricing overall (the dependability factor may outweigh the lower upfront pricing). Being on retainer has an added benefit of staying on clients’ radar for additional projects! You can also find prospective retainer clients from full-time job postings – instead of hiring a full-time staffer and the commitment that requires, they can retain you for a set amount of hours.

2. Build Healthcare, Retirement And Other Benefits Into Your Pricing

One big advantage of traditional, full-time employment over gig work is access to benefits, such as healthcare insurance, retirement plans, paid time off, tuition reimbursement, etc. However, not all employers offer generous benefit packages, so one advantage to gig work is that you can pick and choose the benefits that matter to you. You just need to then build those benefits into your pricing so you can afford to provide them to yourself.

Know Your Top Priorities And What They Cost

When you price and structure your gig offerings, keep your top priority benefits in mind. Know how much your healthcare premiums are, so you can charge each project or client you take on their fair share to cover the premiums. Price for a 52-week year and structure your work over a 48-week period, if you want four weeks of paid time off. Set up your own retirement plan – there are options for self-employed IRA and 401k plans.

3. Reserve Time In Your Workdays For Career-Building Activities

Building a work portfolio that is priced right, strategizing over what clients and projects to take, upleveling your skills for emerging technologies and trends (e.g., AI) — all of these activities are incredibly important and take substantial amounts of time. If you fill your workdays with current clients and don’t reserve any time for career-building activities, your long-term career prospects will always take a backseat and may be neglected altogether.

Plan What’s Upcoming, Review The Past

You can start with an hour on Monday to strategically plan your upcoming week and an hour on Friday to review the past week and identify adjustments needed. Block out increasing amounts of time each week where you don’t work on projects or schedule meetings with current clients. These blocked out times should focus on growing your overall business – sales outreach, pitch meetings, brand-building (e.g., public speaking, writing posts that showcase your expertise).

4. Move Client Relationships Off Gig Platforms

If your gig work is a side project or just one of many income sources you’re juggling, then using gig platforms (e.g., Upwork, Fiverr) are a convenient way to promote your profile and source work. However, you become one of many service providers, and your clients belong more to the platform than to you. You can be negatively affected if the platform changes its fees or service terms, or if your favorite client moves off the platform and you don’t have direct contact with them.

Develop A Strong Professional Network

Always maintain ways that you own and control for prospective clients to find you and hire you directly. This could be as simple as a comprehensive LinkedIn profile that includes contact information and a call to action in your About summary section. If you have work to showcase or media mentions, consider a website. If your business is local, join the relevant chamber of commerce and other professional associations to develop a strong professional network.

5. Set Ongoing Stretch Goals For Project Size, Pricing And Client Pipeline

When you block off time each work to work on your career and not just gig-to-gig, set aside time each month and quarter for longer periods of rest and reflection. Review your business financials, check your client and project mix (are you working with the people you want on the assignments you want?) and brainstorm on what to do next. Set ongoing stretch goals, which could include bigger, more complex projects, landing bigger or more diverse clients, raising your prices or pitching larger engagements (with the higher prices these entail).

Carve Out Your Own Career Path

By continually building in growth opportunities for your gig portfolio, you carve out your own career path. You ensure that you’re not doing the same work over and over, but you’re challenging yourself based on your interests and priorities. This will help you stay competitive if the economy takes a downturn or if a key client goes away (you’ll have others!).