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July 3, 2019

Best and worst things about freelance life

Written by Jack Lewis

Being a freelancer is great. You get to set your hours, work wherever you like, choose who you work with and charge whatever you want for your services. No boss, no horrible clients to deal with and no incompetent colleagues making life more complicated than it needs to be. Perfect.

Unfortunately, a lot of the best parts of being a freelancer can also be the worst parts. Yes, you can work when you want, but only if you can win the work in the first place and motivate yourself to do it. Yes, you can charge more, but you’re also liable for all the costs attached to running a business.

Isolation, inconsistent income and self-doubt can lead to anxiety, stress and loneliness. Freelance life can be an absolute rollercoaster. Often, the dream of what freelance life will be like doesn’t quite match up to reality.

That said, if you can learn to manage the downsides of freelance life, you’ll find that the positives start to outweigh the negatives. In this article, we’re going to look at three things that can be both the best and worst things about freelance life, and how to get the balance right.

  • Flexibility
  • Freedom
  • Finances


One of the most significant benefits of freelance life is flexibility. You don’t have set hours, which makes it easier to work around childcare and other commitments. Unfortunately, because you don’t have set hours, it can be very easy to procrastinate or get distracted. Here are the best and worst parts about the flexibility of freelancing and how to get it right.

Flexibility: The Best Bits

Work where you want

When you work for yourself, you aren’t tied to an office. You can work from home, take advantage of co-working spaces, hire an office, work in-house with clients or work from the beach. It really is up to you.
Work when you want

Choose when you start work, when you finish work, when you take breaks and when to have a day off. The great thing about being freelance is that you set the hours. Of course, there may be times when you have to meet deadlines or adapt to your clients’ schedules, but most of the time, you can work at times that suit you.

Work how you want

You choose your pricing, your packages and your processes, so you dictate how you work. You can use the software, gadgets and systems you are most comfortable with or create your own bespoke systems. You can offer set project packages, or you can work on a retainer basis. Work however you like as long as you can find clients that are happy to agree to your way of working. And don’t forget to protect your business equipment in case anything should go wrong.

Better work-life balance

One of the most significant advantages of working for yourself is that you can fit your work life around your personal life rather than the other way around. Because you dictate when and where you work, you can spend more time with your family and friends. This is especially beneficial if you have children.

Flexibility: The Worst Bits

Distractions and procrastination

When there are no set hours, no fixed office and nobody holding you accountable, it can be very easy to get distracted or procrastinate. Working from home has its good points, but it can also be a minefield of distractions and temptations.

No holiday or sick pay

Being able to choose your hours is great, but, as a freelancer, you only get paid for the work you do. This means that any time you take off sick or for holidays is unpaid. You need to account for this in your pricing; otherwise, you might find yourself working far more hours than you had ever intended.

You can find more advice about setting your rates in our ultimate guide to pricing work as a freelancer.

Loneliness and isolation

Loneliness and isolation can be a big issue for freelancers, especially those that work from home. If you don’t have anyone to turn to in tough times or celebrate your successes with, then running a business can become a very lonely place. Our article about freelancer isolation: how to combat loneliness gives some great tips on how to build connections.

Flexibility: Getting it Right

Be disciplined

Self-discipline and motivation are vital if you choose the freelance route. When there’s work to be done, you need to do it, and if there’s no work, you need to go out and find some.

Set targets, get into good habits, find strategies that work for you. Be strict on yourself, but don’t burn yourself out. Reward yourself for your achievements, even the small ones.

Learn to switch off

One of the biggest attractions to freelance life is that you can work your personal life around your professional life instead of the other way around.

Despite this, many freelancers often find themselves consumed with work, cancelling social plans to meet deadlines, answering emails during family meals and taking client calls on holiday. If you aren’t careful, you can end up working more hours as a freelancer than you ever did as an employee.

It’s essential that you learn to switch off sometimes. An email can wait for a response for an hour while you finish your meal. If the call is that important, they will leave a voicemail or call you back.
Your business isn’t going to collapse if you take a day off.

Just as you need to be strict on yourself with getting work done, you also need to be strict about taking time out.

Have a support network

When you work for yourself, you have successes and failures, you make good decisions and bad ones, sometimes you get it right, and sometimes you get it wrong.

Trying to cope with the ups and downs alone only works for so long – you need a support network. Family and friends are great, but they don’t always understand the ins and outs of freelance life, so you need support from other freelancers or business owners as well. You need people who can be objective or who have had similar experiences.

Whether you find that support through online forums, social media groups, networking events, coaching sessions or industry meet-ups, is up to you. The important thing is building a network of people you can celebrate your achievements with and talk to when times are tough.


Freelancing offers freedom – the clue is in the name. You are free to work with who you want when you want, where you want. You don’t have anyone telling you what to do or taking credit for your hard work. On the downside, you have no support team, so everything falls to you. You might make some great decisions, but then again, you might make some terrible ones. Here are the best and worst bits about the freedom of freelancing and how to get it right.

Freedom: The Best Bits

Choose your projects and clients

As a freelancer, you have more control over choosing the work you do. You can be selective about which clients you take on, rather than having to work on projects that don’t interest you. You get more variety because you work with several companies, not just one employer.

Make all the decisions

One of the biggest frustrations of working for someone else is having no control over how the business runs. When you work for yourself, you can choose where the money is spent, you can pick the suppliers you want to work with, and you can decide what systems and processes to put in place.

All the successes (and profits) are yours

When you work for yourself, the achievements feel more satisfying because they are all yours. Winning your first client, getting fantastic feedback, securing your largest contract to date – each success gives you greater confidence.

The best part is that you reap all the financial rewards. The harder you work, the more you earn – no busting a gut just to come out with the same salary while your CEOs take bigger bonuses each year.

Freedom: The Worst Bits

You have to do everything

Many people go into freelancing with dreams of doing the thing they love every day, whether that’s designing logos, coaching people, building CRM systems, writing copy, bookkeeping or something else.

What gets overlooked is that you need to find that work first. That means doing marketing and sales – it’s highly unlikely that your dream clients are just going to turn up at your door. There’s also a lot of admin involved in running a business – sending out emails, booking meetings, generating invoices, paying suppliers, ordering stationery, managing enquiries, updating files.

Unless you employ a team or outsource tasks, it’s unlikely that you’ll spend every day just doing the work that you enjoy.

You have all the responsibility

Having control over how you run your business is a significant advantage of freelancing; it’s also a disadvantage.

Spending money on the wrong things can be frustrating, and a bad decision can be extremely costly. You can get advice and do your research, but ultimately the choice is yours to make.

When things go wrong, or you lose a client, it’s hard not to blame yourself. Even though no freelancer is perfect, and you can’t win every project you quote for, it’s hard when things don’t go your way.

Having sole responsibility for every decision and every project puts a lot of pressure on you. If you don’t have support or you don’t learn how to deal with that pressure effectively, you can find yourself stressed, anxious and even depressed.

Self-doubt and anxiety

Although freelancing has a lot of benefits, it can also be tough. Rejection, poor feedback and demanding clients can all knock your confidence and lead to moments of self-doubt. The feast and famine nature of work can be stressful; not knowing what you’ll earn from one month to the next can cause many sleepless nights. Running a business isn’t easy, and if you’re doing it alone, it’s even harder.

Our article, freelancer fears: the secret anxiety nobody wants to admit to, gives further tips for dealing with inconsistent income, isolation and imposter syndrome.

Freedom: Getting it Right

Invest in personal development

You might be the best designer in the world or the most incredible bookkeeper there is, but that doesn’t necessarily mean you know how to run a successful business.

Learn the basics of marketing, sales, admin, accounting, customers services and all the other things needed to run a business. Even if you intend on outsourcing, it’s always beneficial to understand the basics so you can make better decisions.


If you aren’t good at something, or you really hate doing it, then outsource.

Why spend hours trying to work out how to do something, when you can pay an expert to do it and focus on the stuff that makes you money instead?

If you can make more money in the time saved by outsourcing a task than it costs you to outsource that task, then it’s a no brainer.

Learn to say no

If you want to work with great clients, then you have to learn to say no to the bad ones. When you are going through a quiet period, it can be tempting to accept lower paying clients or take on projects you don’t really want. Weigh up the pros and cons before you tie yourself into a bad contract.

When it comes to decision making, get advice, do some research, shop around. Don’t rush into decisions about your business systems and processes. Don’t get sucked in by flashy salespeople.

Something might have worked well for other businesses, but is it right for yours?

Think carefully before investing in marketing activities – is it the best use of your money? Meet with potential suppliers before trusting them with your business.

Think decisions through carefully, but once you’ve made them move on. There’s no point worrying about the what-ifs or what could have been. If you make a bad decision, rectify it, learn from it and move on from it.


Money makes the world go round, or so the saying goes. Many freelancers have aspirations of doubling their old salary after they quit the 9-5. After all, you get to keep all your profits when you work for yourself. Well, that’s after you’ve paid your tax, covered all your bills and invested in marketing activities to keep your pipeline full. Here are the best and worst things about freelancer finances and how to get it right.

Finances: The Best Bits

Choose your rates

As a freelancer, you set your rates. Whether you want to charge £20 per hour or £5000 per day is entirely up to you.

That doesn’t mean you should simply pluck a figure out of the air. You can only charge a large fee if people are prepared to pay for it.

Pricing correctly is something that many freelancers struggle with. Many price far too low, which not only makes life harder for them but also devalues the whole industry.

Your price should be based on your talent, not your client’s budget.

Make more money

Because you dictate your rates and decide what to spend money on, you can make more money as a freelancer than you working for someone else. Of course, this is dependent on getting your pricing right in the first place and not spending money on things you don’t need.

If you do get your finances right, then working as a freelancer can be very lucrative. More and more businesses are recognising the advantages of hiring experts on a freelance basis over employing someone to work in-house.

Finances: The Worst Bits

Inconsistent income

‘Feast and famine’ is one of those phrases you hear a lot, but until you work for yourself, you don’t truly understand what a rollercoaster it can be. One month, the work can be flooding in; the next, you can be wondering how you’re going to pay the mortgage.

While you can never wholly guarantee consistency, there are some things you can do to reduce the extremes.

Always work on your sales pipeline. If you only focus on the projects you have, once they come to an end, you’ll have no work waiting for you.

Even when you are busy, make sure you are still marketing your services and responding to enquiries.

Late payments or non-payers can also have a massive impact on your cash flow. If you are struggling to get paid on time, then our guide on how to get paid as a freelancer will help.


You might be able to bill more as a freelancer, but unfortunately, you don’t get to keep it all. As well as paying tax, you also have to cover all your costs. This includes marketing costs, travel costs, equipment costs, supplier costs. If you aren’t careful with your expenditure, you can end up spending more than you earn.

There’s also a risk that things could go wrong. Illness could prevent you from working. A client could decide to take you to court. Your equipment could get stolen, or someone could be injured as a result of your work or equipment. You might not be able to prevent these things, but you can at least prepare for them by getting the right insurance in place such a professional indemnity, public liability and business equipment cover.

Finances: Getting it Right

Set targets

It’s not enough to simply know what is in your bank account. If you want to get your finances under control, you need to understand your income and expenditure, set targets and budget effectively.

Write down how much you want to pay yourself each month, add your fixed costs and set a realistic budget for other expenditure such as marketing. The total is your monthly target. Now work out how to earn this. How many new clients do you need to win or how many hours do you need to bill for? Do you get enough enquiries? How many of those enquiries do you need to convert into sales?

If you know your numbers, you’ll find it easier to forecast more accurately, which will make your income more predictable.

Be organised

Keep on top of your bookkeeping. Pay bills on time and have an effective invoicing system. Keep money aside to cover tax bills, prepare for quieter periods of work and be sensible with what you spend money on.

If you struggle with numbers, then hire someone to take care of your bookkeeping. Work with an accountant to do tax returns and ensure that you aren’t paying too little or too much.

Get the right protection in place. At Dinghy, we offer a range of insurance products designed specifically for freelancers, including professional indemnity, public liability, cyber liability and business equipment.

If you stay organised with your finances, you’ll be able to identify problems before they get out of hand.

Key Takeaways

We hope that this article has given you a good insight into freelance life and some useful tips for getting the balance right. Here is a summary of the key takeaways.

  • Be disciplined with your work
  • Learn when to switch off
  • Build a support network
  • Invest in personal development
  • Outsource when appropriate
  • Learn when to say no
  • Set targets
  • Be organised

About Dinghy

Dinghy was founded by freelancers, for freelancers. Our insurance products are designed to help freelancers ensure the right protection at the right price. We are also passionate about helping freelancers build and grow successful businesses by sharing useful advice and information on our knowledge base and blog. If you’d like to know more about Dinghy, check out our about page where you can meet our founders and read our story.

About Jack Lewis

Read more blog posts by Jack Lewis

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