14 Lessons I Wish Every Freelancer Knew

Here are 14 lessons I wish every freelancer knew:

1. Freelancing is hard.

Anyone who tells you otherwise is ignorant, lying, or trying to sell you something.

2. Freelancing is a game with cash prizes.

Some rules you can’t break—for example, clients must receive equal or greater value than what they pay, or they won’t stay clients long.

Some strategies make the game easier to win and bring outsized rewards—for example, specialization + positioning cheat code + productized services + consistent marketing.

Find the best strategies, and play to win.

3. Quality has become table stakes.

Simply being good isn’t good enough now.

What else can you offer?

And what else? And?

4. Whether you like it or not, you’re in sales.

You must de-stigmatize sales for yourself.

For example, here’s the reframing that has helped me: Selling is bringing clarity and serving.

Every freelancer can learn how to be above average at sales through better consultative technique, not natural pitch ability. Improve your technique proactively.

5. Better questions lead to bigger proposals.

The initial request may not be the real project or the most valuable outcome.

Keep peeling back the layers.

Look for pains and wants.

6. Clients will always tell you what they want to buy and how they want you to sell it to them.

Take careful notes during discovery calls.

Capture their word choice.

Concoct painkillers, not vitamins.

7. Whoever is doing the talking is doing the selling.

Ask the questions, then shut up.

Share new ideas and perspectives, then shut up.

Show exuberant enthusiasm, then shut up.

Active, artful listening builds authority.

8. Prospects can’t get excited if they’re confused.

Use industry jargon like salt and pepper—sparingly.

Too much spoils the dish.

Sell to them in their dialect, not yours.

9. Use a contract to squash ambiguity and protect both parties.

Define key terms (“revision” vs “edit”), what the client gets, what they don’t get, how much it costs, and when they pay.

Tie installment payments to dates, not project deliverables or milestones, because delays they introduce should cost not impact when you get paid.

Ambiguity is the enemy always, not the client.

10. Requiring a deposit keeps both parties honest.

Does the client work for free? No?

Then why should you?

Ignore this advice only when you can afford (literally) to get stiffed, feel confident that you won’t, and see long-term value in having that client’s logo in your portfolio.

11. The client’s budget isn’t your problem to solve.

They dial back the scope to match what they can pay, or they find someone else.

You don’t run a charity.

And you’re not a grocery store that accepts competitors’ coupons.

12. Charging hourly penalizes your skill, efficiency, and expertise.

Track your time obsessively.

Pivot to the flat fee model as soon as you can predict accurately how long certain projects take.

13. No pricing model is “bad,” including hourly.

Pricing models are tools for managing risk.

Pick the right tool, based on the job, your confidence, and your risk tolerance.

As your risk tolerance and confidence go up, you’ll raise your prices and charge based on value.

14. Freelance projects don’t have set prices.

If your prospects can’t pay what you want to make, raise the perceived value through positioning and messaging.

Or, go fish in a different pond. One niche will place a higher value on the same outcome than another.

Some clients in the niche will focus on price. Others will focus on value. Find the latter.

Alright, enough freelance preaching for now. Hope you found something in there worth your while.

(Related post: 12 Pricing Lessons Learned from 13 Years As a Freelancer)

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