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10 common challenges you’ll face as a freelancer (and how to manage them)

By Carrie M. King →

Freelancing offers flexibility, variety, and creative control, but it comes with a lot of challenges. Let’s explore the most common hurdles freelancers face and how to overcome them.

Every year, more and more people decide to go freelance. Statista estimates that the number of freelancers in the US alone will hit over 90 million by 2028, up from 57.3 million in 2017. This steady rise in the number of freelancers is hardly surprising. The global jobs market is increasingly precarious and attitudes to work and its place in society are rapidly shifting.

A career that enables more independence, flexibility, and choice is an exciting prospect, but freelancing comes with plenty of challenges. Our current systems cater mostly to traditional employee-employer relationships and freelancers often lack the support and knowledge they need to navigate administrative tunnels, legal issues, and financial insecurity.

That’s what Goose will be tackling, as we grow. We help you deal with the annoying parts of freelancing so you can focus on building up your business, all while keeping you informed and inspired. Here are some of the main problems that freelancers face.

  1. Finding clients
  2. Getting paid
  3. Handling admin
  4. Paying taxes
  5. Buying insurance
  6. Building your network
  7. Managing time and productivity
  8. Creating a work-life balance
  9. Navigating income instability
  10. Solving legal and contractual issues

Below, we’ve gathered some tips on how to go about solving these key issues. We’ll build up this resource as we grow so make sure to come back regularly for new and updated content.

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1. Finding clients as a freelancer

Want to go freelance but not sure how to go about finding work? Don’t let this question keep you awake at night. There are lots of ways you can go about finding clients.

Need extra help finding freelance clients? Goose has got your back. Sign up here to get notified when we launch—and to nab some exclusive early-bird offers!

Here’s a little food for thought:

  • Who do you already know who might be interested in working with you?
  • Do you already have or can you build up a personal website or portfolio to define your service?
  • Which relevant services, newsletters, and social media accounts can you follow for good opportunity listings?
  • Who are your dream clients and how could you approach them?

Be reasonably wary of large gig economy platforms (which shall remain nameless) as they’re often used to advertise low-paying work. A key part of surviving as a freelancer is in knowing your worth. Do not accept poorly paid work or work for “exposure”. You’ll thank yourself later.

2. Getting paid as a freelancer

Money is a knotty issue that we tend not to like talking about. If you want to freelance, however, you need to get used to having some awkward conversations about getting paid. Late payments can be a common feature of freelance life. That’s why it’s useful to build up a little emergency fund before you go freelance to cushion the blow if a client doesn’t pay on time.

Goose is going to help you get paid. Sign up here to stay up-to-date with pre-launch developments, to get notified when we go live, and to get some special early-bird-only offers.

Here are some ways to minimise late payments:

  • Define a clear pricing structure so you know your rates before you go into any fee negotiations.
  • Agree payment terms with your clients in writing before you start any project.
  • Automate invoices and payment reminders so you don’t have to personally send uncomfortable emails.
  • Make clear from the start that late payments will incur a late fee in the next invoice.
  • Understand your rights and know the actions you can take in the event of unpaid invoices.

Read our full article on getting paid as a freelancer here.

3. Handling freelancer admin

Love paperwork? Well then you’re going to adore freelancing. One of the harsher realities of becoming a freelancer is that you have to handle all your own admin. From invoicing to insurance to tax contributions, once you become a freelancer it’s all on you. Requirements vary depending on where you live, but it can be useful to hire a tax advisor to help you navigate the nitty-gritty.

Here’s a non-exhaustive list of admin tasks you’ll have to take care of:

  • Business registration
  • Contracts and vendor agreements
  • Insurance
  • Invoicing and receipts
  • Tax returns

Need a little help sorting out all your paperwork? Goose can help. We’ll launch very soon so watch this space. In the meantime, check out our guide to handling freelancer admin.

4. Paying taxes as a freelancer

We briefly mentioned it above, but filing your tax return is a major event in every freelancer’s calendar. As a freelancer, you will most likely have to pay your tax in a single lump sum. Before you know how much you’ll have to pay, you need to declare your yearly income to your country’s revenue body. Lots of people employ accountants or use online services to help with their annual tax declarations.

Here are a few ways to make sure you’re ready to file your tax return:

  • Keep a record of your income and invoices.
  • Keep receipts for business-related costs like office equipment, phone bills, client lunches, travel, co-working, or online services.
  • Make note of your registration numbers and tax class.
  • Check your local taxation rules and set aside the required percentage of your income to foot your tax bill.
  • Check if you need to charge and pay VAT.
  • Check if you are entitled to any rebates or exemptions.

Our full in-depth article on paying tax as a freelancer is coming soon. Check back soon!

5. Buying insurance as a freelancer

Insurance requirements differ from country to country, but as a freelancer, it’s extremely important to invest in insurance. Freelancers don’t have the benefits or security that often come with full-time employment, so you need to be prepared for every eventuality.

Here’s a list of some insurances you will likely need as a freelancer:

  • Health insurance
  • Travel insurance
  • Equipment insurance
  • Life insurance
  • Income protection insurance
  • Third-party liability insurance

Full (riveting) article on insuring yourself as a freelancer coming soon.

6. Building your freelance network

While the word networking might conjure up visions of awkward schmoozing, the reality of freelancing is that the people you know are likely to be your most reliable source of work and new projects. The good thing is that you already have a network, even if you don’t realise it. Nourishing your existing professional relationships will pay dividends in the long run.

So how do you grow your freelance network?

  • Tell literally everyone what you do and that you’re open to new projects
  • Reach out to former employers or co-workers
  • Attend events relevant to your industry and talk to at least one person. You never know how that connection may come into play later.
  • Research potential clients and introduce yourself directly and politely over email or LinkedIn.
  • Be genuine in your interactions.
  • Help others who need a hand. What goes around comes around.

Read our full guide to building your professional network as a freelancer.

7. Managing your time and productivity

At some point, most freelancers will struggle to understand how much work they can take on, what their true capacity is, and how to be productive without burning out. It’s normal for freelance work to be a little ‘feast or famine’, so how can you make sure you’re taking on the amount of work that’s right for you? If you struggle with productivity, how can you set up supportive structures for yourself to make sure you get things done? How can you figure out what kind of work motivates you the most? You are your own boss so make sure you act like it.

Here are some simple elements of time management to consider:

  • Be strict about the number of hours you work per week.
  • Make sure you charge enough that you don’t have to run yourself ragged to make ends meet.
  • Overestimate how long it will take you to complete a task.
  • Communicate, communicate, communicate. Make sure your clients have clear expectations and if you run into delays, let them know ASAP to alleviate pressure and stress for both parties.
  • Schedule focus time into your calendar and respect it. Turn off your phone and close your email tab.

Comprehensive guide to productivity for freelancers is coming soon. Watch this space.

8. Creating a work-life balance

Productivity and work-life balance are intimately interlinked. Being a freelancer really underlines that reality. It can be tempting to say yes to every project you get offered when you’re a freelancer but if you do that you may end up burning yourself out. Remember: cultivating a strong work-life balance will make your work better, too. Everybody wins!

Here are a few ways to carve out balance as a freelancer:

  • Schedule your work week and try to stick to your plans.
  • Factor exercise, rest, meals, family, and social time into your schedule.
  • Create strong boundaries with your clients.
  • Take your weekends and holidays off.
  • Charge fees that leave you comfortable enough to take time off.

Want to dive deeper into how to create a strong work-life balance here? Full article coming very soon.

9. Managing income instability

One of the hardest parts of freelancing can be its unpredictability. You might plan for a big project that falls through. You might have a client who refuses to pay on time. You may receive a bigger tax bill than expected. You may simply have a fallow period where you don’t receive that much work. This is difficult both on a very practical and emotional level.

Here are some steps you can take that may help you manage income instability:

  • Set a budget. Knowing how much you can spend and how much you need to earn can help you figure out how to manage your income.
  • Build up an emergency fund. Set aside three to six months of living expenses so you can cover your costs in the event you need to.
  • Speak to a financial advisor. Talk to a professional to help you plan for your personal and professional financial needs.
  • Get insured against income loss. If, for whatever reason, you find yourself unable to work, insurance can help to bridge the gap until you’re back on your feet.

We're working on a complete guide to managing income instability. Come back soon to check it out.

10. Solving legal and contractual issues

The potential for legal and contractual issues are possibly the most intimidating part of freelancing. In fact, it’s one of the key reasons we started Goose in the first place. Any kind of employment is liable to surface the occasional legal or contractual issue so make sure you know what to do if one should arise.

Here are a few aspects to keep in mind:

  • Always read your contracts thoroughly before you sign them. Query anything you don’t understand and ensure you’re clear on all obligations.
  • Sign up for a service like Goose that can handle any legal queries that should arise.
  • Communicate directly and raise any concerns immediately so that issues can be rectified before it becomes a legal issue.
  • Educate yourself on employment law and know your rights.
  • Take out legal insurance which may cover your costs if required.

We're building a comprehensive freelancer guide to managing legal issues. It'll be on its way very soon.

There’s a lot to consider when you become a freelancer, but some research, forward-planning and smart structures will make your life much easier in the long run. We’re working on building up resources to help you manage every aspect of freelancing so keep an eye on this blog for more.

Sign up to get notified when Goose goes live and, in the meantime, let us know what you need support with at suggestions@goosefreelancer.com. We can't wait to hear from you!

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