A push season is the challenging, temporary starting point of working for yourself

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Freelancing is continuing to gain momentum as a viable career path for more of us. One in three skilled U.S. knowledge workers now freelance, says the Future Workforce Index.

That’s due to the instability of the full-time job market and the unique benefits that self-employment can offer, like greater control of your work and schedule. Despite increasing interest and the numerous perks, starting out on your own is one of the hardest parts.

I call this the push season, the initial stage of self-employment that requires a significant effort to attract clients, deliver work, and set up operations for the very first time.

You’ve got to push through a lot of uncertainties. You’re reassessing your professional identity, which can bring up new feelings. You’re also responsible for taking on every function of the business, from accounting to marketing and sales. And most importantly, you’ve got to bring money in the door to ensure it’s a viable venture. It’s a lot all at once.

A push season can be the first few months or as long as the first few years, as you put in more hours, effort, and energy to get to the point where you have a stable income and your business foundations are in order. Ideally, you’re avoiding burning out in the process.

Navigating this push season intentionally can better position you for continued long-term stability as a freelancer. Here’s what worked for other seasoned freelancers and me.

When you first get into freelancing, you’re starting fresh. Yes, this is still the case even if you’re leveraging some of the trust, connections, and experience you’ve built in previous full-time roles. Self-employment isn’t better or worse, just different, as you call all the shots.

It’s going to take time to build up your reputation and relationships around offering your expertise in the form of products and services in a freelance capacity.

This is where you’re building significant momentum around your offerings as an independent contractor. You’ll mainly focus on three key areas: attracting clients, balancing your workload, and structuring your business for longevity.

Bringing on clients requires you to make a consistent effort in marketing yourself to potential customers. This is likely going to take up a lot of time in this initial period.

When I started freelancing, I sent about 20 cold email pitches a week to companies that would benefit from my writing and marketing services. I also messaged colleagues on LinkedIn. That way, they kept me in mind for this type of support I provided, and I regularly shared educational posts on social media to show vs. tell what I had to offer.

Now, some of this is about scale (like how much marketing you’re doing), but most of this effort is about regularly communicating your value to the right people in the right places.

“I had to invest way more time and energy into finding paying work and clients. That’s a bigger time suck than people might think it is,” says Kat Boogaard, a freelance writer of 12 years who sometimes worked 60-plus-hour weeks during her initial push season.

“While I used to spend a lot of time sending cold emails and scouring freelance job boards, more of my work started to come through referrals or other inbound efforts as I got more established,” she says.

Landing clients takes a lot of effort up front, but it is a worthwhile investment. Once you’re established and clients know you from your work, you can ease up on these activities a bit.

Another important aspect is balancing your workload is determining how many projects you need to take on to build financial stability, or in other words, mapping your bandwidth.

At the same time, you don’t want to sacrifice quality or burn out. This will require some trial and error. As you take on a mix of tasks and deliverables for clients, assess (and document) how long it takes you to complete them.

Taking on too many assignments or a project requiring more time than expected led to many long work days in this phase of my freelancing. Limit spells of overworking by giving yourself more runway on each project. This way, you can leave room for downtime between tasks, and thoughtfully increase your pricing over time.

“I didn’t have a good handle on how much I could realistically take on. So, if and when I was able to find work, I often overcommitted myself. I had no choice but to put in long hours just to get it all done by the deadline,” adds Boogaard.

Limit spells of overworking by giving yourself more runway on each project, leaving room for downtime between tasks, and thoughtfully increasing your pricing over time.

Recognize it’s also a considerable mindset shift going from being assigned tasks in a full-time role and being accountable to a boss, to designing your workload without supervision.

“That season was hard. It was raw. It wasn’t just about effort. It was an ego death - letting go of certainty, structure, and the version of myself that once felt safe in systems that no longer served me,” says Mimi Gonzalez, a social impact strategist and Gen Z inclusion consultant, who’s freelanced for three years.

This season requires you to rethink the definition of a career and what success looks like as you transition from being told how to work to designing how, when, and where you work.

You’ll also want to structure your freelance practice for the long term. Many people treat freelancing as a stopgap, which is great if that’s what you’re after. However, if you want to ensure that it’s a viable career trajectory over time, diversification is essential.

This entails finding a mix of clients, supporting multiple industries, or trialing different service offerings. Doing so allows you to gain stability and reduce reliance on any single source of income. At the same time, you’re likely setting up a website, business insurance, accounting system, and the other typical building blocks of getting your practice in motion.

The challenge here is prioritizing these tasks that will allow you to get your business running while making long-term investments in future progress. It’s a constant process, but like any season of freelancing, you’ll move through it.

“Push seasons aren’t one-time events. Every new level of visibility, income, and purpose brings a different kind of push and set of decisions you have to make,” says Gonzalez.

Gonzalez went on to say, “And then there are calmer seasons, when your work carries its own momentum and opportunities arrive because people already believe in what you’ve built. That first push season will always stay with me, though. It required urgency to build visibility and momentum quickly.”

A version of this article first appeared in Fast Company.

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