Map your slow season(s) and adjust accordingly

Howdy! This is Career Freelancer: doable strategies and actionable insights on self-employment as a sustainable, financially rewarding, and engaging career.

Summer has always been my slow season. I see less outreach about new projects, slower communication with existing clients, and everything business-wise feels a bit quieter.

In many ways, it’s wonderful as I’m also a bit distracted by the joy of good weather, going to the pool, and spending time with loved ones who are also amped to spend time together.

This season did freak me out at first as it’s nerve-wracking for things to slow down. And in some years that directly equated to less money coming in.

It felt like it was my fault, and in other moments, I was fearful my business was in a downward spiral. But that never happened.

In the last 13 years of doing my own thing as a freelancer, I’ve come to realize that every business ebbs and flows and this is common, even for very established solopreneurs.

I’ve seen this with big-time authors, well-known consultants, and connected fractional leaders who used to be in the C-suite, who all have moments where there’s a noticeable shift in demand.

Over time, you’ll start to recognize when there’s more demand and budget for what you offer in your industry, whether that’s getting hired for speaking engagements or designing branding assets. Every business, sector, and work product has its own seasonality.

You deal with slow seasons as a solopreneur by mapping patterns in demand for your offerings, planning ahead for these downturns, and taking action when your bandwidth does open up.

The goal here is threefold:

1. Avoid freaking out by recognizing demand will always fluctuate to some degree.

2. Protect yourself financially ahead of these periods, so they’re less impactful.

3. Invest in pipeline tracking, continuous business development, and income diversification to better insulate your business from the effects of seasonality.

You’ll notice the outcome we’re after isn’t preventing slow seasons. That’s not realistic as you’ll always be up against a range of market conditions you don’t have full control over. And demand for any skill set and experience will regularly shift.

What you can do is plan ahead for a known slow season, reduce the number of slow periods, and minimize their impact on your bottom line, well-being, and business model.

Acknowledge the feelings, then shift

It’s more than okay to experience all the feelings during these freelance slumps, but try not to spend too much time being distraught and instead take action based on what’s in your control.

As Barbara Corcoran famously said, “The difference between successful people and others is how long they spend time feeling sorry for themselves.”

When things begin to slow down, acknowledge what you’re feeling but recognize it’s an opportunity to reset and take action.

Examine why the slowdown happened (as best possible)

After you’ve spent time in your feelings, it’s important to consider why this lull in business is happening in the first place.

Way too often do freelancers fill the void by landing new clients and then moving on without much introspection. Reflecting on why work has slowed allows you to address the root causes.

Yes, it’s a difficult problem to diagnose as a solo operator. Sometimes it’s a random combination of factors happening all at once, but often, it’s related to one of the following themes. Seasonality. Competition. Relevance. Visibility. Economic Conditions.

There’s seasonality in demand for different offerings across every type of work and industry, due to regional and cultural norms, and based on how budgets are allocated across the year.

For this one, it simply takes time to get accustomed to the ebbs and flows of when clients are most often ramping up or slowing down their hiring in your sector.

On the competition front, don’t overemphasize this one as it’s more beneficial (and just kinder) to befriend other freelancers than it is to consider them your enemies.

At the same time, recognize that some of the work you deliver might eventually get outsourced to folks with a different cost of living willing to deliver at a lower price.

You may also find yourself aging out of certain types of services, where someone younger with comparable skills is willing to do similar work for less.

The way forward is to keep adapting your offerings and avoid relying solely on execution-heavy work. Support rooted in advising, strategy, and your accumulated industry perspective is far harder to replicate.

Probably the most difficult one to manage is maintaining relevance. At any point in time, there’s cultural shifts, technological advances like AI, industrial consolidation, globalization, and economic cycles shaping which freelance skills and services are in demand.

You can’t control the emergence of these shifts, but you can reactively gain new skills and experiences to meet the moment or proactively diversify your expertise and offerings in a couple of different ways.

Visibility is the most straightforward in that you might not be putting yourself out there enough to stay top of mind with new and existing clients. You likely have talent, experience, and past wins to point to, but without communicating this consistently, the leads might start to slow down.

The solution is investing in energizing marketing that is exciting for you to commit to and of interest to your audience, so you’re sharing your ideas and project wins in public and private forums.

You have no control over economic conditions, which could lead businesses and individuals to tighten their spending for various periods of time. And as contractors, we’re usually first on the chopping block.

This can mean slower payments, fewer projects, and more competition for the remaining work. Again, diversifying your client base across different industries can help make you less sensitive to a downturn. Plus, having a financial cushion is always helpful here too.

Engage past clients for work (a targeted circle back)

One suggested starting point for maintaining cash flow when you start to notice a slowdown is getting back in touch with past clients. They already trust and know you, so the odds of a positive response to your outreach are significantly higher.

Ideally, this isn’t the first time you’ve touched base with them since your project wrapped, as we want to avoid this feeling transactional. That’s a note for your future self to check in with past clients, send them relevant industry news or resources, and just stay in their good graces in a natural way when you don’t need anything from them.

Even if that’s not the case, now is not the time to be modest and hold back. Email or call clients that you had success with on past projects and see if they’ve got any work you can help with.

What you’re asking needs to align with the context of what you do, what you’ve done for them in the past, and what kinds of support they need right now. But you don’t have to predict this, you can ask them directly since you have rapport. Here’s one way to frame it:

A personalized pitch that’s a direct ask if they need more support based on what you delivered before, a recap of the results, and an open-ended ask to see if there are other ways to collaborate. An added bonus is offering a discount for repeat customers, adding some urgency.

Finally, the best-case scenario is to get them on the phone or a virtual meeting to brainstorm in real-time.

Some of this outreach will be ignored; others will say now isn’t the right time, or provide another valid reason why they have to pass, but it’s all worth it to see who’s interested in a new project.

While this is a process you can repeat to your contacts at multiple clients, it’s necessary that each message or call is catered to your history with them and their context as a business.

If they end up not hiring you from this outreach, ask them to keep you in mind as a referral if any relevant projects or opportunities come by their desk in the near future.

Prioritize continuous progress

To move past the tough moments, I usually focus on making continuous progress on meaningful tasks for my business since I have more time to do so—and it feels good.

I’m not alone in this: Professionals have reported more positive emotions on workdays where they made progress on meaningful work, and most often it’s small wins, according to a survey of 238 professionals by HBR authors Teresa M. Amabile and Steven J. Kramer.

For me, this might include small tasks like updating my website, reconnecting with a colleague, writing an article, taking a course, or whatever feels genuinely productive.

You’re not just aiming to be busy but looking for work that helps generate momentum, improves upon your skill sets, attracts more projects, or simply provides creative fulfillment.

I’ve found that this forward momentum helps me move past that stuck feeling and keeps me motivated to forge ahead. I recommend identifying up to five tasks you’ll work on every day and aim for small ones that are possible to achieve in as little as a few hours or a couple of days. The hope is that the continued progress becomes ingrained as a lasting habit.

Expand your freelance offerings and income sources

In the midst of a dip, it might be time to reassess how you’re reaching new customers and whether there’s an opportunity to increase your visibility in a sustainable way.

This could entail building a presence on another destination to reach your ideal like creating a Substack, being a guest on industry podcasts, or speaking at conferences.

Similarly, you might expand your platform as a freelancer to reach a different, complementary customer base with a service you may not have offered previously.

“During slow periods in my business, I try my best to treat it as a strategic opportunity to reflect and iterate,” says Gigi Robinson, a New York City-based creator, speaker, and author.

“Instead of spiraling or stressing about the lull, I dive into my analytics—what’s working, what’s underperforming, and how my audience is responding across platforms. I revisit my goals, experiment with new formats, and map out long-term ideas that don’t rely on external brand campaigns or speaking invites.”

For example, in 2023, she experienced a slowdown in inbound brand deals and speaking gigs. “Rather than panic, I leaned into building something bigger—and that’s when I conceptualized Hosts of Influence, my new educational platform for creators, whether you’re a newbie or a creator veteran,” says Robinson.

“It’s proof that sometimes the most impactful ideas are born when things get quiet. You just have to give yourself the space to listen and come up with a strategic game plan.”

Chart a similar path for yourself by assessing where there’s opportunity to market your services differently and provide new offerings that meet customer demands.

Network with other freelancers

You’re not the only professional to experience a period of stagnation. One of the most impactful things you can do at this point is reach out for help.

That’s why it’s important that you use this time to connect with other freelancers to share how you’re handling it and hear how they’ve dealt with similar circumstances.

Both parties can learn from each other about how to overcome these challenges, brainstorm new opportunities, and provide a fresh perspective on their career trajectory.

You can find other professionals on freelancer marketplaces like MarketerHire and Behance, focused networking groups like ones for independent contractors in HR or engineering, and on Reddit, LinkedIn, and YouTube.

What’s worked for me is building relationships with colleagues who are ahead of me in their career, or I’d like to emulate aspects of what they’ve accomplished professionally.

Through their support, I’ve been able to better anticipate some of the common challenges as a freelancer and get inspiration from how they’ve navigated their career over the years.

The same can be said for fostering connections with new freelancers in their early days of self-employment, as I have a lot of advice and support to offer them.

Plus, these peers often give me exposure to a new viewpoint on the world of self-employment, helping me stay modern, adaptable, and motivated.

Pitch yourself to unlock new networks

One upside of not earning the income you expected is that it can be extremely motivating and drive you to put yourself out there in ways you hadn’t anticipated.

“During a slow period, I reach out to past clients, prospects, collaborators, and peers with one question: “What’s keeping you up at night right now?” Their answers help me spot patterns and spark ideas I can quickly test—whether it’s a new workshop, course, or consulting offer,” says, Hussain Bandukwala, a PMO and project management consultant, trainer, coach, and LinkedIn Learning Instructor.

“I also experiment with different outreach strategies, from lead magnets to paid ads,” adds Bandukwala. “It’s not filler work—it’s targeted R&D to evolve and optimize the business.”

There’s no shortage of ways to do this. One option available to everyone is looking for posts about project opportunities on LinkedIn so you can find the right person to address your pitch to.

The only way to 100% know if someone is looking for freelance support is if they publicize their search or you find out through a referral in your own network.

There’s no shortage of ways to do this. One option available to everyone is looking for posts about project opportunities on LinkedIn so you can find the right person to address your pitch to.

You can certainly look for freelance projects listed on the jobs section and apply to those when relevant. But the better scenario is catering your outreach to the contact who’s hiring for a project, so you’re able to position yourself more intentionally.

Start by searching for posts shared on LinkedIn where someone is sharing with their network that they’re looking for freelance talent for themselves or their company.

Make this happen in the search bar by adding terms like freelance project lead, hiring executive coach, part-time product manager or whatever keywords align with your focus, then filter by posts, and adjust the date posted to the past 24 hours or past week.

Scroll through until you find posts with relevant projects. Now you know who the point of contact is for a project, given that they posted about it.

The goal now is to cater your application directly to this person when you apply, then leave an insightful comment on the post indicating you’ve applied, and lastly, send them a private message with the three reasons you’re a total fit.

The extra effort here is how you make a cold pitch stand out for the right reasons as your outreach is memorable and is getting in front of someone actively evaluating options.

Enhance your skills and expertise (fill a knowledge gap)

During this time, consider whether you’re going to expand your existing services, develop a brand new offering, or pivot entirely to meet demand and prevent more slow periods.

Prioritizing skill development is one way to prepare for this. No matter the industry, enhancing your existing skills and acquiring new, complementary ones is what ensures you remain relevant.

Direct your efforts toward passive and active learning, two modes of professional development that’ll better equip you to stay ahead of the curve in the future.

Passive learning is one-way engagement with educational materials where you’re not immediately applying the learnings, getting hands-on, and engaging with others.

This involves asynchronous courses, reading articles, listening to podcasts, and consuming newsletters, and should be a daily or weekly practice of absorbing new information.

Easier to incorporate into your workday and completely self-directed, you create the curriculum that aligns with your expertise as a freelancer.

Active learning is two-way interactions with instructional materials through engaging with others by discussing, analyzing, and applying the lessons learned.

More time-intensive, active learning happens in cohort-based courses, networking, masterminds, group workshops, coaching, and educational bootcamps.

It’s deeper immersion into the subject matter and is focused on collaborating with other learners, instructors, mentors, or coaches to help explore and integrate the material. Aim to incorporate active learning once a quarter or every few months to explore new skills more comprehensively.

Investing in both types of learning ensures you’re more equipped to adapt your services and better positioned to seize the opportunities that keep your freelance practice thriving.

Embrace expense-covering work (put the guilt and ego aside)

Sometimes it’s in your best interest to take on the work that simply pays your bills in the short-term.

Even if these projects aren’t exactly fulfilling or something you’d normally take on, it’s okay from time to time to prioritize the work that’s low lift, easier to land, and even at a lower rate than you’d usually accept.

While you want to be very careful not to bog yourself down with lots of low-paying gigs that hold you back from bigger, more aligned projects, sometimes expense-covering projects will help you weather the tougher seasons. I’ve done it. Most freelancers have; few admit it.

If this resonated with you, subscribe here for weekly insights on how to maintain a thriving freelance career that’s sustainable, profitable, and enjoyable.