Why freelancers overthink everything (and how to stop)


Hi Reader,

Happy Friday!

Today is the last day you can get early bird pricing on cohort #2 of The Hello Effect. We're already halfway sold out and doors close for the rest of the year on Monday. If you want in, find out more here and then join us here!

P.S. In this week's Instagram post, I shared to grow a freelance business without constantly hunting for new work. Check it out here. And don't forget to give me a follow for regular tips and tricks!


Here's what I've been up to this week work-wise:

πŸ‘‰ I wrote 2 pieces for clients (Modash)

πŸ‘‰ I refreshed 2 pieces for Shopify

πŸ‘‰ I planned an editorial calendar for a new client

πŸ‘‰ I opened the doors to cohort #2 of The Hello Effect

πŸ‘‰ I had a discovery call with a potential client

πŸ‘‰ I had my birthday on Monday!

⏱ Approx hours spent on client work this week: ~18

⏱ Approx hours spent on non-client work: ~3

πŸ’° Total revenue this week: Β£3,055


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Friday Freelance Tip​​ ✨ ​

I'm going to talk about something sliiiightly controversial today.

There's something I see crop up a lot, especially among new freelancers, and that is good ol' overthinking. Some freelancers seem to really agonise over every single word in an outreach email, analyse every single word of feedback a client sends, and spend days trying to figure out what to charge a new prospect.

If this sounds familiar, you're not alone (from a former overthinker) and you're definitely not broken. There's actually a reason freelancers are especially prone to this.

Why we're wired to overthink

There's no one to tell you you're doing fine.

When you work in a company, you get constant, ambient feedback. Could be quick hat tip from your manager or a thumbs-up in a Slack thread, you know the deal. As a freelancer, that feedback loop is barely there, if at all. There's no direct feedback from the decisions you make or someone to say "yeah, that rate sound good" or "no, you should charge more" so we... procrastinate.

Every mistake feels like it could be fatal.

Employees can mess up and survive it. They'll still get their paycheque (unless they've done something really bad). For us freelance folk, it can feel like we're trying to prove ourselves with every single client interaction. That automatically raises the stakes on everything, even things that really don't matter much (like the exact wording of a follow-up email).

You're the only decision-maker.

Unless we have a tight-knit freelancer community around us, we don't really have anyone to run our decisions past. And, even if we do, these people are obligated to help us or even care about the decisions we make.

Uncertainty feels very dangerous.

Freelance income and reputation are inherently uncertain, and human brains do not like uncertainty (cool cool). Overthinking is often just your brain trying to force certainty out of a situation that doesn't have any, so it turns over a decision again and again in the hope that one more lap will help. It won't. There will just be more laps after that.

Rejection hits different when it's personal.

A client saying no to your pitch feels like they're saying "no" to you as a person. That makes the stakes of every pitch, every email, every "can we hop on a call" feel ENORMOUS, which is exactly the kind of thing your brain wants to agonise over in advance.

Why I think this is holding freelancers back

After doing this for a humble 13 years, I've realised that not overthinking things is one of the biggest reasons I've gotten as far as I have.

I definitely don't make perfect decisions. I've got things wrong pleeeenty of times. But making a decision quickly and course-correcting later has, again and again, beaten sitting on a decision until it felt safe.

A few reasons why:

  • Speed compounds. If you make a call in ten minutes instead of three days, you get to the next thing faster. Do that enough times over a year and the gap becomes pretty damn big. Overthinkers aren't slower on one decision, they're slower on their whole trajectory.
  • Most decisions aren't actually high-stakes. The wording of an email. Whether to accept a slightly awkward-sounding project. Whether to reply today or tomorrow. These feel huge in the moment and mean almost nothing in six months.
  • Overthinking doesn't even make the decision better. Past a certain point, more deliberation doesn't get you a better answer, it just delays the same answer you'd have gone for anyway.
  • Clients notice hesitation. Slow, overly-cautious responses read as uncertainty. Clear, prompt ones feel more confident, even if you're basically saying the same thing.

Looking back, there are things I wish I'd just done early on instead of turning over in my head for weeks, a.k.a. pitches I sat on, prices I second-guessed, emails I drafted a dozen times. The version I sent in the end was rarely much different from the first draft. The only thing all that thinking cost me was time and a looooot of unnecessary stress.

What changed things for me was basically realising that not everything is that deep. Most freelance decisions are reversible, low-stakes, and forgettable within a week... to everyone except you, sitting there overthinking them.

How to actually stop overthinking

Set a decision timer. Give yourself a time limit. 10 minutes for an email reply, a day for a project decision. When the timer's up, go with your gut. This forces you to trust your instinct.

Ask: "Is this reversible?" Most freelance decisions are. You can rephrase, follow up, adjust a price, walk back an answer.

Ask: "Will this matter in a month?" Most of the things we agonise over are completely forgotten within days. Save the deep thinking for the handful of decisions that really are big (long contracts, major pivots, big financial commitments, etc.).

Write the first draft and send it. Especially with emails and pitches. Your first instinct is usually 90% of the way there. The other 10% you're chasing by rewriting it five times isn't making it better, it's just making you feel better, temporarily.

Separate the decision from the feeling. Anxiety about a decision isn't the same as evidence that the decision is wrong. You can feel nervous about sending a pitch and still send it. The feeling will pass either way, and it doesn't need to be resolved before you act.

Build a small "just do it" habit. Pick one low-stakes thing a week where you'd normally overthink, and force yourself to act fast instead. Reply to that email in five minutes. Send the pitch without a third read-through. It's a muscle... the more you practice deciding quickly on small stuff, the easier it gets on bigger stuff.

Remember: nobody else is thinking about this as much as you are.

You are, by a huge margin, the person paying the most attention to your own decisions.

As always, happy freelancing πŸ™‚

Lizzie ✨

This week, we have a B2B writer from Germany.

Where are you based? Hamburg, Germany (soon to be Berlin).

How long have you been freelancing? Just over 2 years.

What do you do? B2B writer for tech products (adtech, martech, HR tech), but I’m constantly exploring and on the lookout for more topics. I fell into these categories because of my experience, but my interests extend way beyond that.

What's your revenue? €11,290.

This person freelances part time and this was their highest earning year.

How much did you take as a salary?

Around €5,000 – the rest I used for operational costs, website, training.

How much did you pay in taxes?

€0 – I didn’t earn enough freelancing to pay tax, but I paid more than my fair share of taxes for my full-time income. πŸ˜‚πŸ˜­

What are your business expenses?

€127 rounded up – this is for my laptop lease, Ahrefs, User Metrics and Claude. I have yearly subscriptions for my accounting tool, Screaming Frog, website hosting, Craft (where I store articles I use as inspiration for my own work), a PO box and my tax consultant. I used to subscribe to LinkedIn Premium but honestly didn’t see any value in it. I also had my website redesigned!
​​
Do you contribute to a pension or invest?

I pay a private pension every month, but it’s a pretty abysmal amount. I have another German state pension I pay into with my full-time job.

Any personal money-management or cash flow tip you'd like to share with others?

Ask me in 2 years when I’ve figured it out a bit more. At the moment, I’ve been prioritising the set-up of my business, but I need to get savvier and learn as I go. My freelancing started as something I wanted to do for extra cash after being burned by the lovely UK Student Loans Company, but I’m coming to learn just how much this revenue stream excites me – even if it’s not much at the moment.

We need more Freelance Money Diaries entries! I'm forever grateful to anyone who shares their finances with us (you can do it totally anonymously!).

Click the button below to do yours! of

As always, happy freelancing :)

Lizzie ✨

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