I started freelancing 26 years ago next month. And I’ve been coaching and mentoring other soloists, even informally, for just about as long.
Over the years, I’ve developed a list of favorite questions for new freelancers & consultants. They’re not about the nuts and bolts, like an invoicing system (you need one) or whether to incorporate (you should). Rather, they’re about the big-picture matters that can drive years of success.
Even if you’ve been at it for a while, these are good questions to revisit.
Let’s dig in.
1. Why are you doing this?
Given the infinite number of things you could do with your one life, why did you choose freelancing? What role do you want it to play in the fabric of your life? Are you running to it or running from something else?
Remember Fred, maybe the worst freelancer I’ve known? His freelance origin story was that he was trapped in his office job on a beautiful summer day, and he decided he would rather be outside. This is not an idea upon which a business should be launched.
Better answers will focus on an important intersection: The chance to improve the condition of your clients and your life. The specifics will vary for each of us, but If you do this freelance thing correctly, both parties will be better off.
2. How’s your personal financial picture?
Are you under financial stress, or do you have some runway? What’s your baseline income requirement, and what’s a stretch goal? How many gigs will you need to achieve each goal?
Asking these questions up-front helps you to frame freelancing like a business – which it very much is – and will have a direct effect on the specifics of your plan.
3. What does your ideal engagement look like?
I’ve met far too many soloists who can’t tell me what a great gig means to them.
Define for yourself:
- What kind of deliverables?
- At what rate?
- With what kinds of clients?
- In what conditions?
Not every gig will check all those boxes. But defining a perfect gig is the first step in attracting it.
4. What’s your offer?
It’s one thing to be a designer. It’s another thing to offer “top-to-bottom visual brand identity.”
What exactly are you selling? What do you do that’s different, better, easier, faster or sharper? What does the client get? How are they improved and transformed?
If in doubt, incline yourself towards higher-impact, higher-value offers.
5. How’s your network?
Freelance fact: Most of your early gigs will come from people who already know you and your body of work.
(This may not change much over time, by the way: 95% of my lifetime revenue has come from either repeat business or referrals.)
So, who in your network is in a position to hire you? Who in your network needs your services today? If your answer is “not that many people,” then building your network just became one of your top priorities.
6. How will you find new clients?
How will you let people know you exist? And how will you do this both very well and very consistently?
Some new freelancers ambitiously sign themselves up for a dozen different marketing tactics. I’m here to tell you: You don’t have that much time, and you won’t do that many things well.
“Fewer things done better” is the way.
7. Why should they hire you?
Most of us aren’t bringing something completely new to the world. More often, we are providers of a known thing, even if we put our own spin on it.
In other words: Demand for your services has already been proven, and your job is to harness that demand.
And that’s about credibility. Authority. Proof.
If you’re just starting out as a freelancer, you’ll need to lean on your prior work record – titles held, brands touched, accomplishments earned. Every new gig is a chance for you to develop other kinds of proof: Brand associations, testimonials, referrals, case studies, results, and so on.
And as you consider your marketing tactics, remember: Those that build credibility and authority are generally better than those that don’t.
8. Are you ready to do the whole job?
In my years as the client, I worked with plenty of talented freelancers.
But some always needed their work double-checked. Some couldn’t manage a timeline. Some couldn’t receive feedback well. And those aren’t people I can hire a second time.
As freelancers, we’re also project managers, account supervisors, and quality-control specialists. (Among other things.) It’s not just about “the work.”
9. Who’s on your team?
Friends, this one is not talked about nearly enough.
I use the term “soloists” often – hey, it’s right there in the name of this newsletter! – but to be clear: This is a difficult path to walk alone.
It helps to have:
- A supportive significant other
- A coach or mentor
- An accountability team
- An informal “board of advisors”
I’m not saying it can’t be done otherwise. But much of my growth has been the result of the generosity of others: Their words of support, their perspective and insights, their challenges when I was taking the easy way out.
10. How hard are you prepared to work?
Though I’m distinctly “anti-hustle,” I’ll also say that this is not the line of work for those who don’t want to work hard.
Especially in the first few years, you’ll need to learn to do the work that brings in the work. And you’ll have to do this consistently, even when results don’t appear immediately.
There is no escaping this reality. And those clowns on social media who claim to work an hour a day? They’re selling the worst kind of lie.
11. How’s your mindset?
Are you energized? Positive? Optimistic? Do you believe in yourself? Do you believe you have something to offer the world?
Freelancing will give you plenty of opportunities for dark nights and blind alleys. If you’re not starting out on good mental footing, things can snowball quickly.
On this point, I offer one of my favorite quotes, from Steve Martin: “Through the years, I have learned there is no harm in charging oneself up with delusions between moments of valid inspiration.”
12. What does a good life look like to you?
This is perhaps the most important question. Your freelance business should fit within, and support, your vision of a good life – whatever that means to you.
Ultimately, my business is about facilitating a certain lifestyle. I want to do meaningful work in a healthy environment, and I want to enjoy life outside of work.
And while those scales aren’t always perfectly calibrated, knowing what I’m working for, and toward, makes all the difference.
And there you have it – 12 questions for new freelancers and consultants, or even for those of you who have been in the game a while.
At any given moment, you’re probably feeling good about some of your answers, and not so good about others. That’s true for me too. But if you’re asking the important questions and answering them honestly, you’ll be well ahead of most.
Your time is valuable, and I hope I’ve rewarded it. If so, your shares are greatly appreciated, as I try to spread the gospel to as many freelancers as possible.
I have a limited number of slots available for 1-1 coaching. I’m not some guy who’s been freelancing for a minute – I’ve been doing it since 1997, with brands you’ve actually heard of. Click here to find out more about how my customized coaching can help you level up.
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