5 Unavoidable Obstacles Freelancers Face

It’s been a few months since my last article and I know all 5 of my regular readers are patiently awaiting an update. I transitioned to a new position, at a new firm and the last few months have been hectic. Not that I don’t love it, but it takes a lot of work to build up a solid book of clients and provide them excellent services. For that reason, I wanted to use my recent experience as a launching point into writing for this blog again.

If you work in a typical office environment- stationed before an endless array of screens in a windowless cube, becoming a freelancer might seem like a dream job. You can set your own schedule, work from home, set your own pace and answer only to yourself.

Well, not exactly.

As a freelancer, or really in any client-service-based business, your schedule and pace is ultimately determined by how much of your time you sell. Further, your work location is often limited to where your clients live, or at least within their time zone. And everyone has to answer to someone, whether it’s a supervisor, your clients, your investors or your spouse.

For as far back as I can remember I wanted to work for myself. My first attempt as a freelancer was as a website developer, but I didn’t like how clients constantly requested changes (sometimes unnecessary changes). My next effort was as a private piano instructor and though I enjoyed the freedom and was able to pay my bills, the business eventually plateaued. At that point I could either devote more time, raise my prices or move on. So I decided to try something with better growth potential. Years later, as a tax consultant, my practice now gives me plenty of autonomy and allows me to work with clients from all over the country.  

But it’s still hard! 

The same issues I had as a web designer and piano teacher resurfaced in my taxpayer representation and resolution practice. I began to worry- What if I don’t have what it takes to deliver client services long-term? Instead of fixating on the inevitability of failure I decided to take steps to identify these issues and attempt to resolve them.

5 Unavoidable Obstacles Freelancers Face

#1. Getting New Clients

Before you can show off how good you are, you have to find someone willing to take a shot on you. Actually, you need to find lots of people willing to use your services and if you ever stop, you run the risk of work drying up. And though getting clients is always a good thing, having more work than time can quickly become overwhelming.

Solution: In my experience, unless you have a steady stream of clients you should never stop trying to get more. Once you have more clients than time you may need to hire an assistant but there’s nothing worse than turning down projects because you’re too busy with previously contracted work.

In order to keep your sales cycle rotating and avoid burnout a freelancer must know their business inside and out. How long will it take to complete a project? What is the average market rate for the work? What do you charge for changes or additional work? Knowing these figures will help you prioritize your time and will naturally limit the work you undertake for free.

#2. & #3. Getting paid for your Time and Client Expectations

It took me a long time to realize that what a client says and what they do are often separated by an ocean of uncertainty. Someone may say that they will pay you for additional services only to cancel a check.

Solution: Before you complete any work for a client, you should discuss their goals and your expectations for the completion of  the project. If clients are rescheduling or bouncing payments the first step is to have a conversation with them and restate your agreement. Further, holding off from working on a project until the payment clears is a good way to limit your work load. Sometimes a client will eventually realize that they need the work done and will pay you down the road. For this reason I always maintain solid relations with my clients. If they’re scared to call you because they feel that they owe you money most clients would sooner hire someone else than return to a tainted relationship.

#4. Staying Organized 

I’ve found that the easiest way to juggle multiple client projects simultaneously is to keep  organized. Otherwise, you run the risk of missing deadlines or wasting time reviewing projects/cases.

Solution: A calendar system (such as Google Calendar or Microsoft Outlook) is key to keeping track of all of the small steps you must track for a freelance project to be realized. For each of my clients I have a permanent calendar ‘event’ and I keep detailed notes of all phone calls and actions I’ve taken (with dates and times). That way, every time I open that calendar event, I know exactly where I left off with the client. There are many ways to organize and your business may dictate other requirements. The point is that without being immaculately organized you cannot handle multiple clients efficiently.

#5. Staying Motivated in the Long Term

Staying motivated can be difficult as a freelancer. When clients aren’t returning your calls or have missed payments, things can start looking hopeless quickly.

Solution: I wish I had a one-size-fits-all solution to this problem but there are just too many variables. For me, motivation issues arise when I get tired, bored, or if I feel overworked. Sometimes, I get an urge to drop everything and become a longshoreman. If you can figure out whether your lack of motivation is simply a passing phase- and I’ve found that most are- then you can formulate strategies to combat these phases.

Comedian Bill Burr said this (or something roughly akin to this) on his Monday Morning Podcast: “Whatever it is your doing just keeping doing it and something is bound to come from it.” The path may be tough but the easiest way to fail is to quit.

Then again, sometimes the business you’re in is truly not worth your time, effort or the constant struggles. In my 5 Things Every Business Needs to Survive article I recommend having a well considered exit strategy. If you are experiencing long-term losses, it’s probably time to make some changes.

Do you provide client-services? What advice would you give me?


  1. Ughhh, so much yes with #2 and #3. I think these are the big reasons freelancers stop working or get fed up with everything. People think that they can short change freelancers for some reason, like our time and effort is worth pennies. Y’all: we need to stop undervaluing ourselves just to get clients. That’s the reason we all get paid pennies for our hard work.

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