Why Freelancers Should Strive to ‘Fail Better’

It’s always a risk to start a new business or launch a freelance career. Once you’ve filed all the legal paperwork, you want to focus with laser precision on success, because failure isn’t an option. Everything is riding on you making something of this enterprise.
It’s important to not be deterred by the idea of failure because you learn from every mistake you make. Being afraid of failure means not taking chances or pushing yourself to get better by taking risks with clients, jobs, or even the nature of work that you do.
Let’s take a look at the some of the common ways failure enters the life of a freelancer, and how we can accept our mistakes, dust ourselves off, and jump right back into the game.

What Do We Mean by Failure?

Failure, in this case, doesn’t mean you have to close up shop and return to an office job. It means that something you tried didn’t work out as planned.
Sometimes these unfortunate turns can discourage you and make you second-guess your decisions. They can even make you feel like a fraud.

Instead, look at failures as a chance to change and grow, and “fail better”* the next time.

Let’s take a look at a few examples where you might experience failure, and how you can turn these events around to become a positive experience for yourself and your business.

1. Choosing Clients and Gigs

New freelancers often worry about money. That means you might jump at every potential opportunity that crosses your path. This can lead to overextending your time, and if you’re not familiar with every style or type of gig in your field, you might also vastly underestimate the time and resources you’ll need to complete each opportunity successfully.

The good news is that most freelancers start off as generalists, so you’re in good company. As you gain experience and succeed with certain types of clients or projects, and struggle with others, you’ll discover what works best for you.

Don’t just skip opportunities because they’re challenging, though. For example, maybe you design graphics for websites, and someone asks you to do a book cover. Or maybe you’re a writer and a client asks if you’d be able to put together a slide deck. Even if you’ve never done those kinds of projects before, that alone isn’t a reason to say no.

Pushing yourself is the best way to learn new skills. Each and every gig you take should take you a little out of your comfort zone and force you to take risks in order to learn something new.

2. Pitching Clients

Most freelancers start out writing pitches to random clients with the hopes that the client will like what they hear and hire them. When you send out email after email and never hear back, it can be really discouraging, especially if your bank account is running on empty.

While it might be that another professional is a better fit or has more experience, that’s often not the case. In many cases, it might just be how you approach the client. It could really be just how you frame your pitch and communicate your services.
This is a good opportunity to re-examine what you’re sending out to potential clients. Do you send out your pitch promptly (and reply to questions just as promptly)? Do you tailor your emails to the individual client, and address their specific needs? Do you clearly and concisely explain how you can solve their problem, provide a quick introduction to how you work and include a link to your portfolio and testimonials?  
If you think your emails could be the issue, it might be time to get your pitches reviewed by a fellow freelancer or mentor.

3. Losing a Client

This is possibly the worst failure a freelancer might face. If they were a lucrative contract, you might feel like the end is nigh.

But don’t panic. If a client ‘fires’ you, this is a sad moment but also a golden opportunity. Look at what they tell you, and dig deep to see if you can’t understand their reasoning. Were you always tardy in replying to them? Did you argue with them about the nature of the work? Were you too pushy about invoices? Often these things build over time, and you can see them coming even if you try to pretend otherwise. Try to reasonably assess your role in the ending of the business relationship and resolve to do better the next time around.

And pick yourself up and jump back into the game. With your new skills and experience, you might take the opportunity to refresh your resume or update your website with new portfolio pieces. Reach out to your growing network of fellow professionals, or perhaps seek new clients in the same industry your last client originated.

4. Organize your Time

Once you get a steady flow of work do you find yourself working ridiculous hours to get it all done by the deadline? Worse, have you lost a client by not completing everything on schedule?
It’s hard to know if you’re productive with your time or not when there’s no boss, and most of the deadlines are ones you impose on yourself. If you struggle to get work done, here are some ideas:
To organize your time, and fight the feeling of being overwhelmed:

• Structure your work with a day-planner, online calendar, or bullet journal. Create “work time” and “fun time”. You might also schedule household chores and errands.
• Get out of the house. Co-working spaces offer a lot of the benefits of an office without the tie.
• Write down everything you need to accomplish within a day or week and do the easiest things (like paying bills, making a doctor’s appointment) first. Then prioritize everything that’s left into what needs to be done today, this week, and this month.
• Consider hiring out some of the work. This could be getting a virtual assistant who can answer calls, reply to emails, and handle other administrative tasks. But it could also mean paying for someone to clean your house, or using grocery delivery options to take care of your shopping.

Even small changes like these can open up considerable time for productivity.

5. Not Getting Paid

This is a freelancer’s worst nightmare, and it happens to almost everyone at some point in time. While some clients are jerks and try to get work for free, there are other times when the freelancer may have contributed to this outcome.

Things to keep in mind:

• Clear communication is essential. Be sure to state the payment terms and price at the outset, and include it in a written contract.
• If the final costs ran higher than what you agreed upon, be sure to always communicate the situation as soon as it occurs. Don’t surprise the client with a bigger bill at the end.
• Be sure to invoice properly, and provide multiple options for receiving payment.
• Give clients a few days to pay. Remember that most clients are business-owners themselves. Sometimes they get busy, or life happens. After the payment window has passed, be sure to send a friendly reminder. Most will appreciate your professionalism.
• Never badger them. Sending them message after message begging them to pay you will not encourage them to follow through. If you have strong reason to believe they won’t pay, you may need to consult with an attorney or collections agency.

6. Undercharging

When you just get started, it can be a real challenge to determine how much your work is worth. The hourly rate may be much higher than you’ve ever received from an employer, and you might be afraid to charge too much and not get clients.

A common rule of thumb is that when clients agree too quickly to your rate, you’re probably undercharging. If you think this is the case, consider setting your rate based on the value of the work you’re providing. For example, if your design work or copy will bring your client new customers, consider what each new acquisition is worth.

You also should always factor into your rate expenses such as health insurance, taxes, and other operating costs. If you don’t, you’ll end up losing money at the end of the day.

7. Saying No

Do you feel obligated to go out for coffee with every fellow small business owner or freelancer? Do acquaintances contact you to “pick your brain?” It doesn’t take many of these meetings to fall behind in your work.

Or maybe you just can’t turn down a gig, and you end up with more work than you know what to do with.

When the weight of your job is bearing down on you, feel free to say no. Don’t blow off current clients, of course, but feel free to tell a friend/associate/future client that you don’t have time right now to meet their needs. Most people will respect your time and organization enough to wait until your time is available. And if not, don’t mourn the loss.

8. Taking Risks

Many freelancers play it safe and stick to projects they know they can knock out. Or they sign on with a big client and don’t keep any smaller clients around on the side.

When you get in a rut, you don’t grow professionally, and you don’t learn. It’s important to sometimes pitch for a gig that feels way outside your comfort zone, or that will force you to learn a topic or skill that’s foreign to you.

The same is true about other things you might need to do in order to grow your business. Here are some ways you can take smart risks to build your business:

• Spend a bit of money on Google or Facebook ads to get your name out there and build up your clientele.
• Get out and put yourself out there in front of new people. Attend meetups with fellow freelancers, networking happy hours with successful small business owners, or educational opportunities with marketing professionals.
• Hire an assistant or bring on a partner to share the workload.
• Invest in better technology or software. It may require living on a shoestring for a short time, but will help you compete better in the long run.

Parting Thoughts

At the end of the day, when faced with a choice, always take chances and open yourself up to new things. When you fall on your face—and all freelancers do sooner or later—don’t despair. Freelancing is fun and allows for a lot more freedom, but it also provides far more challenges (often without a safety net) than a standard office job might offer.

The exciting part is that everyone follows this path a bit differently, and in the end, do what works for you.
 
* “Fail better” is a snippet from a longer quote from the playwright Samuel Beckett. The full quote comes from his 1983 work Worstward Ho and reads as follows: “All of old. Nothing else ever. Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”