Before You Start Freelancing, 20 Questions to Ask Yourself
Freelancers dream: taking time to enjoy the view
By Andy Strote From the new book How to Become a Successful Creative Freelancer. Coming soon to Amazon and other online retailers.
If you’re considering freelancing, here are 20 questions to ask yourself first.
1. How Much Do You Have In Savings?
Freelancing is notorious for periods of “feast or famine”. Most freelancers will recommend you have three to six months of living expenses saved for slow times.
Or, if you have a partner with a steady income you can count on, you could get by with less.
Don’t start freelancing, if you assume you can support yourself from day one. Also, prepare yourself for the ups and downs of freelance cash flow.
2. What Services Will You Offer?
Assuming your services include some version of writing, design, or programming, try to narrow your definitions to suit your talents and desired direction.
For example, if you’re a writer, would you rather write 1,500-word articles or short social media campaigns? If you’re a programmer, do you have a platform of choice, e.g., WordPress or Webflow? Define your services so you can target clients that are right for you.
3. Who Will Be Your Ideal Clients?
There are many ways to look at clients. They could be big business, small business, start-ups, government, not-for-profit, local, regional, international, etc.
You don’t have to pick just one, but it will be helpful if you have a focus. Once you work in a focused area, you tend to attract similar clients.
Focus relates to niches, in other words, areas of expertise. When you’re starting, don’t worry too much about your niche. It will likely develop naturally in the first few years.
Learn more about working for your ideal clients.
Here’s a hierarchy of client types, from best to awful.
4. How Strong is Your Referral Network?
When you’re starting, you’ll get most of your work through your network. Your network should include your family, friends, acquaintances, and anyone you’ve worked with previously.
They should all know about your freelance offering. Note that projects won’t likely come from your direct network but rather from people who know them.
Let’s say a friend of your mother’s opens a business that needs everything: logo, website, social media presence. Your mother has a coffee with her friend. They talk. Your mother tells her what you do. The friend calls you. That’s how networks work. And that assumes your mother knows what you do well enough to describe it to her friend.
The bigger and stronger your network, the better.
5. How Will You Find New Clients?
Yes, you’ll want to use your network for new business. But you should also have a website, be active on social media, consider outreach through email, etc.
Think of new client acquisition in terms of fishing and hunting. You can fish by putting out your lures so clients find you (your network and website) or hunt, targeting specific clients on social media and then contacting them. Consider doing both.
Here’s a strategy for finding new clients (Hint: they’re close by).
6. Are You Comfortable Talking About Money?
As a freelancer, you’re running a business. Clients will want to know how much you charge. You’ll have to write estimates and invoices. Some clients will want to negotiate your fees.
It all comes down to getting comfortable talking about money.
Try not to take it personally. In business, money is just a way to exchange time and services. Let’s talk about money now.
7. Do You Have a Strong Portfolio?
You need a portfolio. Prospective clients want to see what you’ve done so they can trust you with their assignments.
But how do you get a portfolio when you’re just starting? Learn how to build a strong portfolio even if you haven’t done any client work.
8. Upwork or Fiverr—Yes or No?
These platforms are controversial among freelancers. Some love them, others hate them. Suggestion: if you’re going to pursue working on them, you have to put in full effort.
You’re competing against the world of talent. Yes, you can succeed, but it will take focus. It’s not something you can do casually.
Here’s how to be successful on Upwork.
9. How Will You Handle Client Communications?
Think about a preference for how you want to communicate with clients. Email? Slack? My suggestion is to have a preference but be prepared to be flexible to meet client preferences.
But above all, anything significant should be in writing, so no rambling phone calls, voicemails, etc. Having it in writing protects both you and the client.
Avoid freelancer burnout. Figure out the best way to work with your clients.
10. What is Your Billing Strategy?
There are numerous ways to bill for your work. Many freelancers start off billing by the hour or, if they’re writing, by the word.
But there are other ways, too. You can also quote by the project or use a retainer model.
Think about it, but don’t worry too much. You can change how you bill if necessary. That’s quite common.
Here are the best pricing models for creative services. Which one(s) will work best for you?
11. What Contracts Do You Need?
I’ve never wanted dense, detailed contracts written by lawyers. I had simple Terms & Conditions that addressed payment terms, service terms (mostly about revisions), and any required legal terms, typically addressing copyright ownership.
These Terms & Conditions were included on every estimate.
No contracts or agreements are bulletproof. I never wanted terms that would require a lawyer to enforce. Learn why contracts won’t protect you, but you need them anyway.
12. How Will You Manage Your Time?
Working freelance means that you’re working on client business, taking care of your admin work, and prospecting for new clients. You’re a one-person business, and you’re wearing all the hats.
That means you have to be efficient with your time. You’ll be juggling the various tasks throughout the day and week.
Think about what works best for you. Are you a morning or late-night person? Do you want to do your invoicing as soon as you finish a project or save it for the end of the week?
It pays to know yourself. It’s the secret of running a successful creative business.
13. What Admin Tools Will You Need?
For every task, you’ll have a selection of tools and software that you could use. My suggestion: start simple and cheap. Be sure your admin software doesn’t become a project of its own.
Here’s an example: some people love Notion for the 101 things it does for their business. It’s way too complicated for me, and I’d be spending hours or days configuring and learning how to use it. But that’s up to you.
Here’s how to keep your freelance start-up costs low.
14. Where Will You Work?
Some people need the structure of their own workspace where they sit down at their desk every day. Others can work from the kitchen table. Still others work in coffee shops or shared working spaces.
And then there’s the dream of a laptop on the beach in Bali.
Also, consider noise and music levels. Some freelancers want silence (me), while others can work to music or tune out outside noises.
Think about it and decide what works best for you. You can always change your mind.
15. How Will You Manage Your Finances?
If you’re organized, have a head for numbers, and are comfortable doing your taxes, you can do this yourself. Keep in mind that it will add to your admin time.
You could also hire a part-time bookkeeper or accountant to take care of this.
In any case, don’t ignore your finances, especially the taxes part.
Here’s why I think freelancers need an accountant.
16. What is Your Vision for Freelancing?
For some people, freelancing is a side hustle to their full-time job. For others, it’s their full-time gig. Some people want to work 20 hours a week. Others want to fill 40 hours.
Right now, your goal may be just to get your freelance career underway. Or perhaps you’re looking to grow freelancing into an agency.
There are many ways to do this; the best part is that you can always change your mind. It’s your business, your life.
Know yourself—it’s the secret of running a successful freelance business.
17. Your Work/Life Balance—How?
This is worth thinking about. It’s easy to have your work consume your whole life, especially at the beginning. But, if you have a partner or a family, this will not go over well for long.
From my experience, you’ll be juggling. There will be times when you’re working evenings and weekends. But don’t let your work take all of your time and energy. Pay attention to the rest of your life. It goes by quickly.
18. How Will You Stay Competitive?
I assume that when you decided to start freelancing, you determined that your skills were good enough for the market you want to serve.
But the market changes, so you’ll have to change with it. You may also want to upgrade your offering to clients. That might take some courses or certificates. Make sure your skillset stays relevant.
19. What Will You Do When You’re Not Busy?
There are two aspects to this. First, when you hit a dry spell, you may have little or no money coming in. That’s why you want a cushion of savings. Secondly, how will you use that time to find more clients?
Ideally, you will have a to-do list of tasks to tackle during slow times.
Here are three things you can do when you’re not busy:
Review your existing clients. When did you last speak to them? Let them know you have time available.
Look at your clients to see whether a niche is forming and how you can expand on that. Learn all about niches here.
Review your admin processes. Here are some tips on streamlining your admin processes.
20. How Will You Measure Success?
The obvious way to measure success is through gross income. However, you may also want to consider how many hours it took to earn that income, the quality of your clients, the length and depth of client relationships, and the time you’ve kept for yourself and loved ones.
Some freelancers like to formalize this by setting goals for themselves. Others do it by feel, deciding on any given day how happy they are with their situation.
Think about your goals and what it will take to consider yourself successful.
New Book For Freelancers
I’ve just published How to Become a Successful Creative Freelancer. It’s the essential business guide for freelance writers, designers, developers, filmmakers, and photographers.
Whether you’re just starting as a freelancer or have years of experience, you’ll learn a lot from this book.
It’s broken down into easy-to-understand chapters with strategies and tips you can use today. Not just “what to do”, but also “how to do it”.
It’s available now in Kindle ebook and paperback on Amazon.
Want to Grow An Agency? The Agency Book is For You
If you’re looking for tips on how to build and grow your agency, you’ll want to read How to Start a Successful Creative Agency.
Available at Amazon (Paper & Kindle), Kobo (ebook), Apple Books (ebook), and Gumroad (PDF).
The book is packed with useful information to help creatives start and grow their business.
Continuous Stream of Best Practice Advice
“I love @StroteBook’s continuous stream of best practice advice for #freelancers. Especially his comments on long-running clients: one of my clients sends my Mum flowers on her birthday.”
Steve the TechWriter OG, Twitter
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This chapter covers essential areas such as Clients vs. Projects, Corporate Clients vs. Small Business Clients, How to Create an Opportunity Document, Benefits of Finding a Niche… and much more.
Questions? On Twitter, I’m @StroteBook. D.M.s are always open. Ask away.