The Principles of Successful Freelancing

Miles Burke
Miles Burke

What will you call your business? Will you work full-time or part-time? How will you fit out your office? What are your best strengths as a freelancer? In this sample chapter from Miles Burke’s new book, The Principles of Successful Freelancing, we’ll learn about some of the questions you’ll need to ask – and answer – before you embark on your new adventure.

The most exciting and eagerly anticipated phase of freelancing happens after all the planning – and we haven’t quite reached it yet! There’s good reason for putting the brakes on until we know exactly where we’re going – a freelancer who has built a solid foundation of planning has a far better chance of surviving than a freelancer who hasn’t prepared for the plunge.

In this chapter, we’ll walk through a couple of options for heading down the freelance road, we’ll make a start on the planning by looking at some elementary tools, and we’ll establish the all-important goals and milestones.

Then we’ll consider your trading name, create your start-up shopping list, and contemplate your business structure. We’ll wrap all this up by discussing how to choose suppliers and whether you should consider outsourcing any bookkeeping and additional legal work.

Deciding How Far to Jump

Now that you’ve made the decision to become a freelancer, we’ve reached the point of short-, medium-, and long-term preparation. If you’re anything like me, you’ll want to jump in running as fast as you can. However, it’s been proven time and again that to ensure the best chance of success, you should expend plenty of effort in planning and preparation. This raises the question of which work mode to begin your freelance life with: full-time or part-time.

If you’re a student nearing the end of your studies, you’ve got a distinct time to work towards. (That said, I recommend that unless you have run a business previously, don’t go freelance straight after graduating – spend some time in employment in your chosen field first, to get those skills polished.) This also applies if your current work is coming to a close – you may be on a fixed-term contract, or the company you’ve been working for is winding up. However, for many people, the entry to freelancing is a case of juggling full-time employment with preparations to exit the rat race.

There are advantages and disadvantages to both situations, and you’ll need to weigh these up carefully. Let’s take a moment to look at some of them.

Freelancing on the Side

There’s a lot to be said for freelancing “on the side,” at least in the beginning:

  • This is a great way to test the waters without making that big jump.
  • You can spend as much after-hours time as you need on planning your business.
  • You can save just-in-case money for as long as it takes for you to feel comfortable before venturing into the unknown.
  • You’re able to be choosier with the work you take on, as your salary is still coming in to help with costs.
  • If you don’t have any good recent work to show, part-time freelancing allows you to build a great portfolio before you move to full-time.
  • The clients you groom now are likely to be with you once you make that leap, helping with immediate cash flow.
  • It allows you to take your time to fit out the home office, without blowing your starting budget.
  • Freelancing part-time after hours, as well as holding down a full-time position, gives you the authentic taste of a busy week as a freelancer. This can help you determine your ability to cope with that amount of work at any given time.

There are a few disadvantages to this practice, though:

  • Depending on your employment contract, you may be restricted from doing work that directly competes with services offered by your employer. It’s best to approach your boss to discuss this.
  • Most clients will want to contact you during their workday hours, which tend to be when you’re busy at your full-time gig.
  • You lose out on the all-important downtime hours of evenings and weekends. If you attract lots of work, you may end up exhausting yourself trying to work two jobs.
  • You’ll be cautious of growing too fast, given you have restricted hours in which to work. It can become tricky trying to keep everyone happy, and you may have to turn down new work in order not to fail existing clients.

Freelancing Full-time

There are some compelling advantages to jumping in with both feet:

  • You’ll have the freedom to set up your freelance life, instead of juggling it with a full-time job.
  • Full-time start-up mode means that you have plenty of time in which to network, make important contacts, and meet prospects.
  • There are no issues with your employer being aggrieved about you working freelance on the side, and you’ll have no hesitation in taking on as many new clients and projects as you can handle.

There are, however, some disadvantages to full-time freelancing straight away:

  • Nothing feeds self-doubt more than work failing to come in during those first few weeks.
  • The cash drain while you rush around making contacts and courting business can really hurt your back pocket.
  • The all-important planning tends to be the first casualty when those projects come in – understandably, you’ll be more interested in taking an opportunity to earn some much-needed money than mapping out your legal business structure.
Taking Time to Plan

“Failures don’t plan to fail, they fail to plan,” says best-selling author and business motivational speaker, Harvey MacKay.

If you are planning to start freelancing part-time, you should have the time to put together all of the plans and start saving for the just-in-case rainy-day money. On the other hand, if you plan to move straight into full-time freelancing, remember that you’ll have those looming deadlines as soon as you take on projects. Even so, it doesn’t mean that you should ignore planning or preparation.

For most people, the concept of business planning is likely to provoke a jaw-dislocating yawn. However, it’s much more productive to welcome this as an exciting time, where you start to understand where you really want to travel on this freelance path. The world really is your oyster – you’ve made the emotional commitment, perhaps you already have some prospective clients lined up, and you may have already done much of this planning work in the back of your mind. It’s invaluable to take a little time to write these thoughts and plans down, for future reference and as a way to refine and catalogue your thoughts.

Many freelancers and small businesses fail in their first few years, and it’s widely agreed by experts that the number-one reason for such failure is because those business had little or no form of planning. This planning document doesn’t need to be a huge tome of numbers and words; it really is the summation of what you have been thinking, committed to paper.

This document is where you start to list known and unknown areas of your plans, so you can elaborate on them over time. A good business plan is an evolving one, so don’t consider it a chore to be completed in an hour and then stuck in a desk drawer and forgotten about.

There is a myriad of web sites dedicated to sharing templates and ideas about what they consider a great business plan. Perhaps the most important element of a business plan is that you remain actively involved with it. Review it frequently, adjusting and editing it where required – especially during those first few months.

Your plan could be just a few pages, or it could be dozens, but unless you have grand plans to circulate it for investors or financial institutions to read, avoid using buzzwords and reams of useless blue-sky figures. The plan is for your eyes only, so keep it succinct and to the point, and an honest appraisal of the “who, what, when, and how” of your plans.

There are many elaborate methods for writing a solid business plan, but let’s start by creating a text document, and answering what questions we can from the list in Example 1, “Business Planning Questions”. For those questions to which you don’t know the answer yet, just write the question, reminding yourself to add that material as you go.

Remember, plans change, so at this stage your efforts are likely to be more crystal-ball gazing than actual fact. You’ll expand on the plan, filling it out in more detail as you work your way through this book and progress over the first weeks and months of freelancing. And it’s fine to add other notes besides the questions included here – even if they’re rough dot points, the more notes the better!

Creating a SWOT

The planning term SWOT first appeared in the 1960s. A SWOT analysis is really just a simple strategic planning method that helps evaluate projects and businesses. It’s based around a four-square grid, shown in Figure 1, “The SWOT grid explained”, which covers Strengths, Weaknesses, Opportunities, and Threats. I’ve used it a number of times to help me make decisions around new products or service offerings under consideration, and it works just as well for business models.

Example 1. Business Planning Questions


  • What is the initial concept?
  • What is your current situation?
  • What will your key success factors be?
  • What are your longer-term vision and goals?

market analysis

  • What does the current market look like?
  • What is your target market?
  • What are the characteristics of your perfect client?
  • What do your target clients require?

competitive overview

  • What does your industry look like?
  • Are there many competitors?
  • Who are your five closest competitors?
  • What products or services do they offer?
  • What opportunities do you have to be unique? (Can you fill a niche or be different from your competitors in some way?)
  • What are the risks and threats?

sales and marketing

  • How will you attract clients?
  • How can potential clients find you?
  • What marketing activities would you consider?

plan of action

  • What do you need to do in order to kick things off?
  • What should you do in the medium term?
  • What are some longer-term plans?

Figure 1. The SWOT grid explained

The SWOT grid explained

To start your own SWOT analysis, list all of your strengths and weaknesses – these can be thought of as the internal elements, over which which you have some degree of control. Continue by identifying all of the opportunities and threats that you can – these are generally external forces, such as competitors and the industry at large. Then, look for ways to use your strengths, improve on your weaknesses, exploit the opportunities available to you, and fend off the threats.

A SWOT analysis certainly doesn’t need to be as long-winded as it may sound; I have found some of the most useful SWOT analyses are those that fit onto a single page. By way of example, let’s look at our very own Jacob and Emily.

Jacob has put together the beginnings of a SWOT, which looks like this:

Table 1 – Jacob’s SWOT Analysis
Strengths Weaknesses Opportunities Threats
natural networker (great with people) small savings, and has never run a business before knows the industry, has a good understanding of market many freelancers work nearby
fantastic portfolio of work not proficient with code has many contacts who may be prospects larger firms offering a similar service

Emily, on the other hand, has put together a SWOT that is more like this:

Table 2 – Emily’s SWOT analysis
Strengths Weaknesses Opportunities Threats
has a wide range of skills not very good at planning only web developer freelancing in her local area other people becoming freelancers
very hard working perfectionist; sometimes takes more time to complete projects than she intends to has a contract or two already lined up lack of clients in small city

These examples are only a few lines long, but you can easily extend them to a page or more. The concept is really a succinct and useful method of establishing your pros and cons.

Establishing Goals and Milestones

All this talk of business-planning documents and SWOT analyses may be making your head spin, and you’re forgiven if you find yourself glossing over them in your rush to make a tangible start on your own business. However, I strongly suggest that you take a moment to write down some simple goals and then define some milestones.

Goal-setting helps filter all of the thousands of thoughts and ideas you have into a list that’s far more manageable. High achievers in every field from sports to business consistently suggest that goal-setting is an invaluable part of the process. Goals can help you define your objectives, help you to understand what’s important to you, motivate you towards achievement, and build your self-confidence.

I find goal-setting is most helpful in distinguishing what’s important and what’s irrelevant. This helps me concentrate on what really is crucial to me, and gives me the freedom to spend less time on the rest.

Many people use the acronym SMART when creating goals, as well as for other project management methods. SMART stands for:

  • Specific: is the description of the goal precise?
  • Measurable: do you explain how you will measure results?
  • Attainable: is it possible to achieve, with some effort?
  • Realistic: do you have the power to control the results?
  • Timely: do you have a deadline for the goal?

The reasoning behind SMART holds that a vague goal is an almost useless goal. As an example, say I needed to win more projects; I could define a goal as, “Get more web site projects.” Sure, this is better than nothing, but how much more inspiring would it be if I changed it to say, “Win five more web site projects this quarter.”

See the difference? I’ve been specific (I want to win more projects); I’ve been measurable (I want five more in the next three months); my goal is attainable (who couldn’t win five projects in three months?); my goal is realistic (I know I can deliver five projects within that time); and it’s timely (it has a three-month deadline).

Setting a great goal should challenge and stimulate you. If I downsized my goal to winning one project in the next two months, I’d be more likely to slack off. It also needs to be realistic, though, so some impossible expectation of getting ten projects in three months would set up almost certain failure. It’s a good idea to limit yourself to just a handful of short-term and medium-term goals – writing an exhaustive list of everything you would like to complete prior to your death is a sure way to demotivate yourself.

Tip: Goal-setting Help
You may have heard of the popular Web 2.0 application, 43 Things. This site presents a great example of goal-setting at work – try listing your goals on 43 Things, or simply use a text file or whiteboard, and see how you go!

Now, when we think of milestones, we normally recall a large web project we’ve been involved in. Think of a milestone as a landmark towards your longer-term goals.

A typical milestone is to realize a situation where you’re earning more than your current salary within a year of going solo. There are some smaller milestones you can place along the way to see how you’re shaping up.

The first milestone would be having the ability to pay yourself enough to survive on. Let’s say that’s about half of what you earn today. Set a milestone based upon how long you believe it should take to reach this point – it may be a month, or perhaps three months, depending on your situation.

Now, let’s consider your return on investment, which is initially to reclaim all of those start-up costs involved in your transition to freelance life. These vary, of course, from person to person, but you should have an idea of how long this would take.

The third milestone is that of bringing home the same salary as you currently earn. Will this take six months, or nine months, or even longer?

Write down your milestones and refer to them over the coming months – you’ll be surprised how quickly you reach them, exceed them, and find yourself setting more goals for future success!

Planning the Start-up Shopping List

An important element of this big planning phase you’ll need to do before (or while!) you’re making your move to freelance is to start preparing yourself for some of the expenses you’ll be faced with over the first few months.

Now, I’d like to say there won’t be any costs, but that’s simply not true. However, I can say that shopping around for the best deals, looking for opportunities to swap services with suppliers, and staggering your expenses will certainly alleviate the sting of spending money when all you want to do at this stage is earn a little.

There are immediate costs, depending on your current situation, and then there are costs that you can delay for a while. The best method of allowing for these costs is to create a list, prioritize what you need in which order (based on your current situation), and then expect the higher end of the price range. That way, when those costs work out to be cheaper than anticipated, it’s a bonus for your bottom line.

“Must have” costs include:

  • business card printing
  • domain name registration
  • web site hosting
  • telephone costs
  • hardware
  • software licensing
  • legal or licensing costs

“Should have” costs include:

  • insurance for office contents
  • income insurance or business continuity insurance (if you’re able to be covered)
  • office equipment (desk, chair, light, filing cabinets, printer, and so on)

Ideally, you would cover these costs at the same time as the must-haves, but the reality is most people won’t be able to take such a budget hit in their first month of freelancing, so they can be slightly delayed.

Tip: Thrifty Bargain Hunting!
Don’t forget how much cheaper it is to seek out second-hand office furniture and equipment – you can find bargains through the likes of eBay, your local trading post, or used furniture stores. You can set yourself up with perfectly functional trappings at a fraction of the cost of all-new, shiny furniture.

“Nice to have” costs include items such as:

  • new hardware
  • dedicated servers
  • magazine subscriptions
  • industry association memberships

These would be great if you have the capital, but they can easily be delayed if circumstances dictate.

Through good planning and careful attention to your cash flow, these costs won’t have as much impact as they may seem to have now. We’ll go through finances in more detail in the next chapter.

Note: Leasing versus Buying
When it comes to any high-investment equipment you might need, leasing is a well-known method of improving your cash flow by paying a far smaller amount per month over the life of the lease.

Although the end result is that you pay more for the equipment than if you bought it outright, the benefits of having more cash on hand can be an excellent compromise. You’ll often be surprised at the small difference in final figures, and realize the benefit of being able to hand the equipment back or upgrade it at the end of the lease term.

Creating Your Brand: the Preliminaries

We’ll talk more about branding yourself in a later chapter; however, it’s very important that you carefully consider the business name you plan to use, when first kicking off your freelance career. There are two typical approaches: use your personal name, or create an entirely new trading name.

Let’s look at these options in more detail.

Using Your Own Name

Using your own name is a fantastic way to build a personal brand. Taking this option depends on what your vision of the future looks like – if you plan to hire staff at a later date, you may want to avoid using your own full name, but there are still options available even if you do; for example, Burke Design & Development; Miles Burke & Co. On the other hand, if you have every intention of remaining a one-person show, giving yourself a name like “XYZ Corporation” can be considered misleading, as it won’t take long for your clients to realize that you’re a solo worker.

Note: Anything’s Possible!
Many people start off never expecting to take on staff. Don’t rule this out, unless you feel strongly against it. I once couldn’t picture myself hiring employees … and at the time of writing I have 16!

This theory assumes your name is unique enough to be memorable, and that it’s easy for your clients to pronounce. If your name is Bob Smith, you may find that it’s too common for business registration and other registrations, such as domain names or intellectual property.

To recap, the advantages of using your personal name include:

  • it builds a reputation around you
  • it’s normally easier to recall, since clients already know your name
  • it can avoid misleading clients if you plan to stay solo
  • it looks far more personal and (depending on the uniqueness of your name) can make you easier to find on the Web

Disadvantages of using your own name include:

  • it limits you in terms of hiring staff and possibly even selling the business, if you reach that point someday
  • it can make it harder to rank on search engines if your name is very common
  • it may be hard to pronounce if your name is very uncommon

Using a Fictitious Name

Irrespective of the business structure, having a business name unrelated to your personal name has a number of considerations that need taking into account.

A business name which when read phonetically is still pronounced correctly is perfect. Pfizer could be a challenge; Sigma is fairly unambiguous. Don’t get too clever with creating crazy business names – most people would regret having to answer the phone with the greeting “Smelly Shoe Design” before long.

Having your main service as part of the name makes sense as well, although be warned against making it too specific. For example, perhaps you’re a designer whose short-term plans are to design web sites only. You’ll need to consider whether you plan to expand into other forms of design in the future. Having a name like “XYZ Web Design” when you’re pitching for a logo design project may not help you beat your competition, so beware of suggesting that you’re only capable of providing one service.

A good business name should be easy to recall, evocative, pronouncable, and unique. You’ll want to register the domain name, so run a WHOIS on your shortlist to rule out those already registered. Don’t just consider your own country extension – register as many extensions (including the top-level domains, .com and .net) as possible.

Warning: Unexpected Domain Names
Take a step back and look at your domain name carefully! There’s been more than one business that has come up with a great trade name and bought the (in)appropriate domain name to match:

  • Experts Exchange:
  • Therapist Finder:
  • Powergen Italia:

The advantages of creating a new name for your business are:

  • It keeps your personal and business lives further separated.
  • It allows infinite choice of business name.
  • It allows you to tailor the name according to domain name availability.
  • It’s easier to sell your business or client base in the future.

Disadvantages of using a custom name include:

  • You’ll need to exert some energy to get a new name to stick.
  • You could have issues finding one that you feel comfortable with and fits you well.
  • It’s not an easy process to change the name later on.

If you do decide to use a created name, start by creating a shortlist of options, and then create a spreadsheet. Populate the first column by doing a WHOIS search and finding which domain names are still available (both geographic and top-level).

Table 3 – Business domain name matrix
Name .com .net .us
XYZ Design Factory available available available
XYZ taken taken available
XYZ Web Works available available available

Then, fire up your favorite search engine and search for those business names. What are the results? You wouldn’t be the first start-up to make it this far, only to find another product or business using the same name. It’s better to do this research now, rather than when the business cards have been printed … Try predictable misspellings of the words, too – often a business name may be only one letter different from another, so make sure you check first!

Thirdly, consult your local trademark database and see if there are any trademarks of which you need to be aware. Even very similar words may be worth avoiding.

You should also speak to some friends and colleagues. Ask them what they think of each name in your refined shortlist, and narrow this list down even further. It’s better to do this face to face to observe an immediate reaction, rather than by email or phone, where they may have a longer time to consider it – you want their gut response.

Finally, go with your instinct. After all, it’s your creation, and you have to like it. If, after hours and hours of soul-searching, you just aren’t happy with your choice, try again or consider using your own name.

Example 2. Bam Creative
When considering my own business name, I had a multitude of options. I liked the idea of incorporating my name in the business identity; however, I did want to leave my options open in case I ever hired staff.

Although my name (Miles Burke) is fairly unusual, the domain name was taken at the time, and I didn’t want to tie it in so closely to me in any case.

My initials are MB or MAB in full, and I didn’t believe these really stood out. However, when you reverse them, you end up with BAM, which I felt suggested impact. I knew that Bam was a very popular word, though, so I assumed there was no chance of getting those domains using it by itself.

Although most of my work at the time was web site design and development, I was occasionally brought in on corporate identity design or consulting projects. I’d already decided that I planned to stick to creative work, so I ended up choosing the business name Bam Creative.

This allows my business to work on anything from web sites to logos and anything else that can be broadly considered creative, and still be true to the name. The word Bam is generic enough for most people never to make the connection that it’s someone’s initials, and certainly not the reverse of someone’s initials!

Funnily enough, I did manage to register the domain, but I had no chance of getting any top-level domains (.com, .net or .org). Luckily, I got the full bamcreative business name versions of these.

Considering Your Business Structure

When setting yourself up as a business, you should consider the implications of different business structures. If you intend to take on staff within the first few years, you may wish to set up a corporation. If you plan to remain a solo worker, having everything set up as a sole proprietorship may be the best solution.

Having said this, consider speaking to an accountant and possibly a lawyer to seek advice about your particular scenario. You could also speak to local business bureaux (such as SCORE) or associations. They’ll take into account your current personal and financial situation, as well as your legal jurisdiction. Requirements for different business and company registrations will vary depending upon your location.

Each different structure can have a considerable impact on your taxation benefits, your licensing and governmental costs, and your ability to grow the business in the future.

The main differences between a limited liability company (an LLC) and a sole proprietor arrangement reside in the varying levels of possible taxation benefits, legal protection, ability to obtain finance, and your legal requirements.

Setting up an LLC structure has both advantages and disadvantages. The advantages include:

  • greater legal protection – If a client sues the company, only company assets can be seized to pay any judgement, not your own car or house.
  • greater ability to obtain credit – Many financial institutions and lenders have a preference for a company, rather than an individual, for business finance.
  • tax benefits – In some states and locations, a company receives more taxation benefits than a person.

This option isn’t entirely free of disadvantages, of course. An LLC costs money to set up, and there are ongoing company-related fees. Also, financial reporting is usually more involved than for an individual.

Being in a sole proprietor structure has its fair share of benefits, mostly to do with cost. When compared with an LLC, there’s less financial reporting for most situations, fewer start-up administration costs, and not as many licensing or business costs.

There are disadvantages though, which are easily recognizable as the other side of the LLC advantages:

  • zero legal protection – If a client should sue you, the court can order that your assets be taken to pay any legal judgment.
  • less access to credit – Business loans are likely to be harder to get for a sole proprietor than for an LLC.
  • tax burdens – You may be taxed more than if you were a company.

Ideally, whatever structure you create now will mean that you aren’t paying more than you need to in fees and costs, yet allow you to be flexible enough to accommodate change as your business and your direction evolve.

It’s also a very good idea, regardless of your structure, to open a bank account for your freelance business that is separate from you as an individual. This way, you can pay yourself as if you were an employee, and allow a small nest egg to grow in the business account for those quieter months.

This account will also be used to pay all of your running costs, making the bookkeeping side of your new venture easier to manage.

Speak to as many other freelancers and small business owners as well, and ask them how they set up their own structure – people will soon tell you the pros and cons of their decisions, and this can save you a fortune in reorganization in the future.

Engaging Assistance

Early on in starting out on your own, you’ll want to make alliances and choose suppliers for those services or products that you don’t offer yourself.

A word from the wise: be very careful when choosing a supplier. Using a third-party product or service for a client project is akin to offering a raving endorsement about them, so it’s important to consider your options before making your decision.

As your freelance business grows, you will find yourself using a multitude of suppliers. You’ll find that whole areas of your business rely on them, and they in turn will benefit from the business that you bring them.

You’ll need a domain name registrar, a hosting company, an office stationery supplier, a printer for business cards or other printed matter, and possibly an accountant or lawyer – or both. There will no doubt be other suppliers along the way. And then, of course, there’s the large question of outsourcing – as we’ll see, it’s a false economy to spend time struggling to fulfil the complex requirements of thorough bookkeeping, to use a common example. There are experts to do it quickly and easily while you devote your time to the work at which you excel and that makes you money.

Spend any amount of time on web-based forums frequented by freelancers and you’ll inevitably find discussion threads regarding freelance tales of woe – freelancers losing all of their data as a result of using the cheapest hosting company they could find, or having suppliers directly contact all of their clients, offering to undercut their best deals.

Note: Lessons Learned
Don’t leave backups to your hosting provider. Regularly back up client sites, just in case – this may save you in the future!

If you’re going to resell third-party services or products, ensure that you have a written contract stating what is acceptable and what isn’t. The last thing you want is for your hosting company to go directly to your client base and offer them a great deal to cut you out of the picture.

Do some online research, and read up on the experiences other freelancers have had with the suppliers you have under consideration. Forums such as Web Hosting Talk (see the Reseller Forum) and the SitePoint Forums (see the Web Hosting Forums) have plenty of posts pertaining to which hosting companies treat their resellers well, and which don’t.

The same approach applies to most suppliers you’ll require – there are domain name registrar reviews, printing company reviews, and plenty of other sites and forums to be found.

Once you have chosen a supplier, I encourage you to build a real rapport with them – a great relationship with a supplier can be worth a fortune in a time of crisis, or when you need something done absolutely drop-everything now.

Asking for Advice

One of the disadvantages of a freelance life is working in isolation. You won’t have a team around you, and at times you may feel as though you’re the last person on earth.

This is even more obvious when you realize you probably don’t have someone to give advice. Sure, your partner or family can help to a degree, but they can’t answer questions about your chosen profession in any great detail, unless web expertise runs in the family.

Look through your contacts, and see if you know someone who would be able or willing to play an informal mentoring role. You may be surprised as you look through your contacts on social networking sites or in your address book as to who could give you a hand; it’s often even more surprising how willing people are to be helpful.

Look for freelance or web industry groups that have meet-ups. There are groups like Refresh, Port80, BarCamp, web design meetups, and more, where you can mingle with like-minded freelancers to share stories and ask for advice.

If there are no obvious candidates among your contacts and no local groups, make contacts through discussion forums and your extended networks, or even consider starting your own group. A buddy system between other freelancers, or with a mentor who’s been doing the freelance or small business gig for a couple of years, can provide an invaluable sounding board and information source.

Important: Remember to Have Fun!
There may be times ahead that will make you feel overwhelmed by the mission that you’ve chosen to undertake – juggling money, being a salesperson, working late at night, and seemingly never stopping or being free of responsibility for your business.

However, make sure you take time to look at your achievements, the hurdles you’ve crossed, and the exciting road still in front of you. Freelancing is a rewarding career choice, and allows a level of flexibility that you’ve no doubt dreamed of.

Take time to have fun, pat yourself on the back regularly, and know that the start-up phase is the hardest part – it will become easier and more enjoyable as you travel along this path.

Tip: The Pick-me-up List
Keep a list of recent goals you’ve achieved on a sheet of paper stuck up near your desk. On those dark days when you feel like nothing is working, read the list and reaffirm your progress so far.

Case Study


EmilyFor the last few weeks, Emily has spent a few hours most evenings reading up on business planning, and getting a grip on what she believes are her development areas around her business administration knowledge. Not only has she been furiously reading blogs and discussion forums on this subject, Emily has also managed to scour her local library for relevant books to read on the train.

Emily has written the shell of a plan, and as she makes decisions, she adds them to this file. Although she has some savings behind her, Emily is using spreadsheets to keep track of what expenses will crop up in the first three months, and is working to allow for them as soon as possible.

After much deliberation, she has decided since most of her work will actually come from other web companies and freelancers, and she is certain that she’ll never have any staff working for her, that she’ll use her name as her trading name. Emily has a friend who is a graphic designer, and she’s asked him to work up her stationery in exchange for some web development work for one of his clients.


JacobJacob has grand plans, and hopes to hire an office and employ staff within his first year. Since trialing a few names with friends, Jacob is down to two contenders, and has decided to spend a few weeks weighing them up before making a decision.

Meanwhile, he has surveyed a few friends about their hosting suppliers, and already has contacts at a local printer for when he is ready. A work colleague has offered to do the development for Jacob’s web site, in exchange for cash.

Jacob is keen to start telling all of his contacts his plans, but also knows he needs to hand in his resignation first and get everything sorted – he’s worried that when he tracks down some leads, he won’t even have a business card ready to hand them.


It’s been quite a whirlwind, taking in all the far-ranging subjects of this chapter as you prepare for the complexities of freelance life! The approach to getting the ball rolling is as simple as jotting down your thoughts into a simple business plan, and writing a short list of goals and milestones to work toward in the next few months.

We discussed putting some serious thought into naming your freelance enterprise, and preparing to spend some money on a few staple business purchases. You also need to consider your business structure; making bad decisions now could have long-term and possibly expensive repercussions in the future.

We dealt with looking for suppliers whom you can trust, and considered the benefits of handing the painful paperwork over to a professional who can do it better than you can, and probably cheaper too. It’s also worth looking for someone who can be your informal coach or mentor – their advice will be invaluable to you.

Finally, remember to recognize your recent achievements and have fun!

Now to the thorny subject that lies behind all enterprise! In the next chapter, we’re going to take a look at the lolly, spondulicks, moolah, greenbacks, cashola – in other words, money.

Hooked? If you enjoyed this chapter, you’ll love the rest of the book. In Miles’s new book, The Principles of Successful Freelancing, you’ll learn how to start your freelance career on the right foot. Grab a free preview today!