The Big 3 Questions to Start Freelancing

Don't get bogged down in the unimportant details - these are the questions you need to answer to set your freelance business up for success.

Congratulations, if you opened this article you're probably considering taking the leap into freelancing. But, you're probably finding that there are simply hours of important-feeling minutiae you can use to procrastinate this transition. When I first started, I spent weeks researching the ins and outs of corporate structures and sole-trader regulations and rebuilding my website, all to avoid facing down these important questions.

But what your corporate structure looks like or what framework your website uses won't matter one jot if you give up on self-employment after two months because you never found a single client. Instead, you need to step back and think of freelancing like running any new small business. And that means taking the time to build a business strategy by asking yourself three big questions:

1. What is my product?

If you were starting any other business, this would be the obvious question to start with. Freelancers need to ask this, too. So, what is the product your business is selling? Do you know how to build a data science pipeline in a fortnight? Can you design a beautiful brand page? Do you know the ins and outs of building and releasing iOS apps? Do you know how to set up a marketing dashboard so it looks like a big company's dashboard? All of these are valid sales propositions and every one of them is a real world example I have seen land contracts for myself or my friends.

So start with the raw resource from which you will craft your freelance business: yourself. Write down the things you have been paid to do in the past, the things you know well enough to do as a job now, and the skills you could learn in a month of practice. What sales pitch can you craft from these ingredients?

As you craft your pitch, keep in mind that freelancers come in three main varieties. You can use these archetypes as a foundation for your pitch:

  1. The semi-automatic freelancer is all about doing small projects with a quick turnaround. They often achieve this through the use of templates and libraries and prebuilt elements. This kind of freelancing is great because if you get it right it verges on printing money - a well-automated workflow can handily pull in more per year than either of the other archetypes. The brand page designer sample pitch is a semi-automatic freelancer I know.

  2. The permalancer is all about finding open-ended contracts where their drive and/or expertise provide ongoing value for a client. This kind of freelancing is great because ongoing roles can be structured as a monthly fee or retainer, meaning this freelancer has the steadiest income of the three types. However, it is easiest to become a permalancer if you have some specific knowledge or skill that you can pitch to a client - for example the iOS app example sales pitch is a permalancer (it me!). Being able to spin your skills as expertise gives your client a clear reason to stick with you long-term rather than bouncing between freelancers on shorter-term contracts.

  3. The project freelancer is the go-to person for a larger project - one that might take anywhere from a couple weeks to 6 months. This is the easiest archetype to sell because it's what people naturally think of when they think of freelancers: the artisan who can drop in to craft a website or design an app and then ride off into the sunset. In reality, though, the best part of this kind of freelancer is how freeform it can be. You can craft a project freelance role to fill any niche imaginable between the permalancer and the semi-automatic. Both the data scientist and marketing dashboard example pitches are project-based freelancers I know.

2. How will I reach my customers?

If you were starting a normal business the next question would usually be "who are my customers?" But you're just starting as a freelancer so let's be honest: you probably aren't too picky so long as they can pay you. You can carve a customer niche once your business is established so you can skip this question for now. Instead let's carry on to figuring out how you'll reach those customers. This varies pretty radically based on the kind freelancer you're aiming to be.

The semi-automatic freelancer needs a torrent of work coming in but can compete on price. For this kind of freelancer, high-traffic marketplace sites like Fiverr and Upwork can provide the necessary traffic to find customers, even if they come at the cost of much more intense competition with other providers. Your main risk here will be finding ways to stick out in the marketplace so people choose you.

The permalancer needs only a couple of new contracts every year, but each one must be high value. Even though it sounds very "business school" to say so, networking is a necessary tool for the permalancer. The permalancer's most certain way of finding work is the referral - whether it comes from past clients, friends, coworkers, or random people you meet at events or on social networks.

The project freelancer sits between these two again. For this freelancer as well, networking can be a great tool. But unlike the permalancer, the big project freelancer can also drum up business through agencies and agency-like platforms. Agencies are great because they do the client acquisition and negotiation for you. Search around, find some agencies in your area or whose work you admire, and send them a portfolio of your work. Ask them to keep you in mind if they need someone to do whatever your sales pitch is. Similarly, use that portfolio to apply for "team on demand" networks like Fiverr Pro, Gigster, or A.team. Because you'll need more incoming work than a permalancer, having access to sourcing services like these is often worth their price of admission.

3. What are your Plans B, C, and D?

Great. You've taken the step back to build an actual business strategy. You know what you're selling, you know how you're selling it, and you're sure to have totally smooth sailing from here.

Just kidding. Things will obviously go wrong. They always do. That's why you need to know what your backup plans are. You don't want to wind up in crisis if some part of freelancing goes sideways. Even if you never need these backups, you'll perform your job with more confidence if you have the certainty that you could survive losing a contract negotiation or having a contract cancelled.

Let's start with the most obvious potential crisis - plan B (for Backup) is what you'll use if you wind up with zero or almost zero customers. What could you change to find more customers in a pinch? Do you know some people personally or locally for whom you could do discounted work to beef up your portfolio? If you have a job right now, can you start building up your freelancing business at night while keeping that day job? What forums or events could you join where people who need your services hang out?

Next, what is your plan C (for Cash)? Is freelancing going to bear the weight of supporting you financially? How much money do you need your freelancing to make? What will your prices be? How much work do you need to find to make those numbers work? How long could your savings survive a work drought before you'd be in crisis? Knowing these numbers and keeping track of them is life and death for small businesses and your freelancing work is no different.

Finally, what is your plan D (for Disaster)? Let's assume plan B fails to drum up enough customers and plan C shows that you're running out of money. Or what if something disastrous happens, like you become seriously ill out of the blue and can't do your work anymore. What is your disaster plan if you're facing down a crisis? At what point do you need to call it quits and find a traditional job? Should you get better health insurance than you were going to? I hope you will never need plan D, but it is good to spend 30 minutes thinking about it so that you can embark on the entrepreneurial adventure of freelancing without fearing that it will leave you destitute.


The Core Lesson of Freelancing

Underneath this process lies the core lesson of freelancing - one that took me almost a year of freelancing to internalize myself:

You are a business unto yourself.

It is critical that you think of yourself as a small business when embarking on any journey of self-employment. If you're coming from any number of years working a normal job, this can be a jarring shift. Before you were probably told you were "part of the family" and plied with benefits like health insurance. Now you're a freelancer, and that lays bare a core conceit of capitalism: your time and skills are a product that you're selling. To be blunt, this is true whether you're a freelancer or a full-time employee. The hardest thing is making sure you are getting a fair price for it. The simultaneously scariest and most empowering thing about freelancing is that you have the responsibility and power to set that price.

So remember this lesson, build your business strategy, and put yourself out there. You have skills that people want to buy, you just need to find a way to sell them. You will make mistakes as you try, but the good news is that freelancing contracts expire and you can move on, learn, and avoid those mistakes next time.

Good luck and let me know your freelancing experiences and questions down in the comments.

Catalin Pit's photo

Great article, Zack Sheppard! Thanks a lot for writing it!

Rosius Ndimofor's photo

beautifully written 👏🏾

Tracy Nuwagaba's photo

Nice article

Petr Zernov's photo

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Revon's photo

This insightful article especially for those who are planning to shift from a corporate career to a freelancing career. It is necessary to have Plan B, C, and D as shifting to a freelancing career will be a tough one. Yes! Thank you for this article!

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