How to Be a Successful Freelancer – Rough Guide to Survival in the Self-Employment Wilderness

How to be a successful freelancer
How to be a successful freelancer is a question asked by most people when they consider leaving their day job for self-employment. When you were first considering your freelancing career, you may have dreamt of the freedom of setting your own hours, working from home or your own small office, charting the course of your business, being your own boss. These are some of the main reasons one-time “cogs in the wheel” become freelancers. It’s a good life if you can make it work then keep making it work. The key to success is knowing how to survive.

Running a freelance business has its challenges. It’s like “Survivor”. If you use ingenuity, work hard, and try different things, you won’t be voted off the island. If you know how to handle the hardships and obstacles to success, your freelance business will succeed. Following are typical challenges faced by most freelancers (at one time or another) and possible solutions.

It may seem a little odd that someone blogging for online accounting and finance software, has advice about freelancing. It’s not odd, really. I freelanced for many years. Furthermore, Flare Cloud Accounting was made for self-employed professionals and micro-businesses. Flare’s creators are also free-spirited entrepreneurs (much like you) who want you to succeed. We believe our accounting and finance software can be a part of your success equation. Now onto that freelance survival list 😉

Challenges and Solutions for Surviving as a Freelancer

Running out of cash

Running out of cash is a common problem for many freelancers, particularly those just starting out. Cash flow problems can be an issue for many reasons: too many expenses, outstanding invoices, too few clients, too long to complete a job so you can get paid.


Shorten invoice terms

It’s important that your customers pay you as soon as possible. If you don’t set payment terms, start now. Shorten the payment term to Net 15 or Due Upon Receipt to get that money in your bank where it belongs!

Take some money up front and require milestone payments

Consider requiring an up front partial payment before you commence work and milestone payments over the course of the job. Many freelancers do this. It solves two problems. First, you get some cash in the bank, and, secondly it provides incentive for the client to continue paying. They are less likely to pull the plug mid-job if they’ve made up-front or milestone payments.

Create a budget to know what you spend and earn

Create a budget and know exactly what you spend an earn in an average month. A budget forces you to really SEE how you are spending your hard-earned cash.

Examine then eliminate and/or reduce expenses

All too often, self-employed people don’t review expenses until something goes awry and it’s too late. A monthly review (using a budget) is a good way to keep yourself and your spending in check before problems arise. Examine monthly expenses and answer the following questions:

  • Can you use cheaper vendors/sub-contractors?
  • Could you negotiate better rates or payment terms with vendors?
  • Is your cellular bill too high?
  • Do you have monthly subscriptions that you never use, seldom use, or could do without?
  • Are too payments hitting the bank at the same time? If so, would spreading payments out help the situation?

Outsource some work

Sub-contracting may seem counter-intuitive but you can free up a lot of time that you can then commit to higher value jobs. Consider outsourcing some work to new freelancers who need the work and may not charge as much as seasoned self-employed pros. Hire subcontractors from outsourcing sites like, Upwork,, and If you are a freelance creative you may find these sites particularly useful, but they can also save you time by taking over business administrative tasks.

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Monthly income is variable

For most freelancers, monthly income is variable. You can’t count on a fixed steady income like you did when you worked at your day job. It depends on how many clients you have and how much work you can attract. It also depends on what you charge for services and whether you have a steady, dependable stream of income from monthly services.


Start your rainy-day fund now!

Save some money each month. When business is good, put more in your rainy-day fund. Save a few months of income over time. It will take time and sacrifices, but, once you’ve reached your rainy-day fund goal of 3 months income saved, you’ll have some peace of mind and can survive for awhile if things get tough.

Know the minimum you need to survive.

Can you make ends meet in a “worst-case-scenario” month?  As mentioned above, a budget will give you the data you need to take an unflinching look at income and expenses. You may not want to know, but you need to know. Answer the question “What is the least amount of money I need to survive each month”?

Try for longer-term contracts or monthly service packages

Provide monthly service packages if you can. If you provide marketing, blog writing, massage, house cleaning, personal training or other personal services, provide your clients incentive to purchases long-term service packages.  Either have clients enter a long-term contract where they pay you monthly, or, have them pay you for 6 months of services up front at a reduced rate. You might consider providing a discount as incentive.

Clients take too long to pay

Clients taking time to pay is all too common in the freelance world. There are several things you can do to remedy the problem.


Beware being “too” chummy with clients

Sometimes, freelancers develop closer, more personal relationships with clients than larger businesses. This can be beneficial but may also has a downside. A “chummy” relationship may make you hesitant to behave “like a business” when you need to. Freelancers can benefit from adopting a more business-like attitude toward clients. While remaining friendly is important, be aware that a casual or informal way of relating to clients can also be detrimental.

Take a percentage up front

This was also one of the solutions provided for increasing cash flow. If you take a percentage up front, your client is making a commitment to a project. It also reduces your risk if they are late paying the full invoice.

Provide a discount for early payment

If you provide an incentive, such as a discount (either on the current work or future work) clients may be inclined to pay early.

Don’t hesitate to resend invoices

Send the invoice. Wait until a week before the due date and resend with a reminder. A couple of days before the payment is due, resend the invoice again. The squeaky wheel gets the grease…or payment. Many freelancers are hesitant to “bug” clients. Freelancers must get over their hesitancy to behave in like a business. You are a business. Think about what happens when you are late with a household payment (your phone or electric bill for example). You fully expect the cellular or electric company to resend the bill or even call if you are late paying the bill. If your client is late paying an invoice, they will expect a reminder.

Can’t work from home but can’t afford an office

If you are new to freelancing, can’t afford your own office and don’t have a space to work from home try these alternatives.


  • Shared office
    Shared offices are more affordable. Either share the office with a few people who work part-time, or, share a space with one or two other people. Google “shared office space [ your city name]” and you’ll find many shared office possibilities. Remember to check Yelp and Craigslist.
  • Work at a coffee shop
    Most coffee shops have free WIFI. As long as you are purchasing something (coffee, a sandwich etc.), you can sit at a table and work for hours. If you feel uncomfortable spending an entire work day in one coffee shop, spend a few hours in two coffee shops.
  • Work at the public library
    Public libraries, like coffee shops, have free WIFI. Unlike coffee shops, libraries are quiet which makes them a great place to work!

Can’t afford advertising

Both print and online advertising can be very expensive. There are many avenues of free marketing other than print or display ads.



Don’t count Craigslist out. It’s free, and, you can advertise each of your services. You must republish the ad each month but that takes seconds.


Like Craigslist, Kijiji’s free ad service is an excellent opportunity for freelance businesses, and you can create an ad for each service you offer. Depending on the category, you must republish your ads every 3 months.


Creating a Yelp listing is free. For premium services that guarantee exposure, you pay per click. Start with free ads.

Your website

Assuming you have a website, learn the basics of search engine optimization (the art of getting your website found in Google and other search engines) and social media marketing. You can save a lot of money doing your own web marketing and being found in Google search will increase leads substantially. If you don’t have a website, get one. Try or for affordable WordPress installation and customization services.

Business cards

Business cards are cheap to have made and easy to distribute yourself. Leave them everywhere! Here are few places to distribute a handful of business cards.

  • Friends and family
  • Coffee shop community bulletin boards
  • On car windshields
  • Doctor’s office waiting rooms
  • Public lounges (airports, train and bus stations)
  • Taxis
    Talk to a cabbie. If they own their own cab, they may let you place a handful in the back-seat coffee cup holder for a small fee.
  • University/college bulletin boards
  • Hotel, motel tourism card racks
  • Art galleries and museums

Bumper sticker or cheap vehicle ad

If you drive, get a bumper sticker or cheap vehicle sign. Display your company name, list of services, phone number and website address.

Your Turn! Share Your Solutions to Freelance Business Challenges

How do you survive as a freelance business owner? Share a challenge and a solution.



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