Freelancing For The First Time - A Short Guide For Strategists

Freelancing strategy sounds cool. But is it really what you need to do right now?

Freelancing-A-New-Life-Or-A-New-Limbo.jpeg

Freelancing strategy sounds cool. It can give you a break from a toxic work life, help you meet new companies, and give you back your life, but it can also keep you in a sexy limbo that can prevent you from doing the harder work of examining what you really want in life and how you’ll go about it making it happen.

Here are sixteen thing to contemplate before and as you freelance.

1. Work out why you want to freelance

There are at least five reasons people freelance:
A. “I don’t like being an employee.”
B. “I have to until I get a job.”
C. “I feel disillusioned and want some time out.”
D. “I want more time for other things.”
E. “It sounds cool.”

Be clear or use each interaction with a potential hirer to get clear on why you want to freelance.

2. Consider for how long you’ll freelance

There are at least six time horizons:
A. “Until I like a company”
B. “Until I get a job offer”
C. “Until the economy recovers”
D. “Until I work out what I want in life”
E. “Indefinitely”
F. “For life”

Knowing this will help you make decisions from a place that honors you.

3. Work out how much money you need over what time

This might seem obtuse and difficult but there are rules of thumb. For instance, some people set out to earn enough money to only require about 5% of it per year to live on.

This might be a long journey for you but it helps to be clear on the journey.

4. Revisit your attitude towards materialism, wealth, and spending

It’s easier to do this as you become clear about why and for how long you want to freelance. You might need months of savings and really low expenses during difficult times.

It’s not that these need to be in place before you freelance and, then, at all times, but it’s something to work towards.

The Sweathead Strategy Summer Camp is live. How much strategy can you learn in 100 days? Find out. (P.S. "Strategy Is Your Words" will be available in August, 2020).

5. Think about whether freelancing is really solving the problem you want to solve

Unless you have a big network, reputation, and commercial nous, freelancing can feel like being an employee but with less impact. It’s common to see people alternate between full-time roles and freelancing because they want more authority to make good work happen rather than just coming in and leaving at a reasonable hour.

What’s your mood?

6. Consider whether you’re putting yourself into limbo

Freelancing can seem cool but it can put you into limbo, where you’ll bounce between contracts and phases without work. Challenge yourself to think about what’s attracting you to it and whether you’re avoiding more difficult decisions or challenges that scare you.

7. Work out what you do and for how much

Grab a piece of paper and write down your philosophy, process, and three packages with prices. This is for your eyes only. It will help you work out what you’re about and what you think it’s worth. It will also help you judge opportunities.

As you become comfortable with what you’ve written down, you can choose to share it with prospective hirers.

8. Pricing and payment can take many shapes
A. Benchmarked hourly rate - ask around
B. Company tells you what they’ll pay
C. Project or value-based rate - a flat fee or % based on what you think the work is worth
E. You make up a number that scares you
F. Day or weekly rate - work out how much money you want to earn per year and how many days a year you’ll work then arrive at a day rate.

How you price yourself will depend on


Be clear on payment terms. Ask for some money up front. Treat each project as a way to learn.

9. Document and manage your scope

Most companies will push you through their systems - procurement, NDA, Master Services Agreement (MSA), Scope of Work (SOW), invoicing, and timesheets.

You’ll need to manage your scope, review agreements, and advocate for your payment terms.

You can try to charge money or provide discounts depending on payment schedules and whose legal and scoping documents you use.

10. Company systems exist to dumb down everything

You don’t need to accept anything. You don’t have to sell hours. You don’t have to do timesheets.

You don’t have to agree to wait three months before payment.

If it becomes a deal-breaker, then you have a decision to make - how badly do you want the work?

11. Set up a company if you see yourself freelancing for several years

A company is a useful legal and tax instrument. It can also help you look bigger than what you are and give you a way to get distance from yourself if you start to take business too personally.

12. Build your name and vibe

Selling strategy can take time. Chances are someone will know you or they’ll have heard of you over the years. They’ll keep an eye on you. Then an opportunity will arise and it might take weeks to months to go from the initial contact to meetings and scopes.

If you have a presence and reputation, two things can happen:
A. You’ll attract people who want what you do and how you do it
B. You’ll attract people who’ll take care of you within their systems E.G. They’ll explain things to procurement.

Clients who act like allies within their own systems are beautiful humans. Treat them well.

13. Don’t fear taking the lead

Buying and selling strategy is an ambiguous affair.

Let someone tell you what they want but search for the problem they want to solve and then tell them how you think you can get to the solution.

This means changing conversations from “We need a planner for two weeks” to “This is how I can help solve your problem.”

14. Embrace selling

You might get repeat clients but chances are you’ll often need new clients. So stay active in public. Negotiate credit for your work and whether you can show it in public. If you can’t share the work you do then this reduces your value over time and you might want to increase your fees.

Selling and negotiating make freelance life happen so try to enjoy them.

15. Launch strong and stay front-of-mind

There are no right or wrong ways to launch yourself as a freelancer but don’t underestimate launching strong - have a solid website, a good social presence, an email list, and clear ways of working.

Create something worth sharing. There’s a buzz you’ll get a few shots at over the years but launching well is important. Then stay in public.

16. Keep an eye on fantasies and flattery

“I’m going to set up a collective.”

“All these people want coffees.”

“Yes, you can pick my brain.”

These are common distractions.

Remember, a lot of successful business people see other people as something to operate or to extract from. Have a focus, an intention for what you want to do in life. It will help you work out what to say “Yes” to.

You can also find this article on Instagram.