10 lessons on freelancing

Today marks the 10th issue of Rough Draft. 🥳

Thanks for being here! I genuinely appreciate every single one of you. There are countless newsletters out there and the fact that you have subscribed to mine (and stuck around for 10 issues!) is an honor.

I don’t take my position in your inbox lightly. I want to make sure I’m delivering value to you so you have a reason to stay subscribed.

So tell me: What freelancing topics do you wish were talked about more? What burning questions do you want answered?

Don’t be shy! Feel free to reply directly to this email with your questions or feedback. I reply to every one 🤝

10 Lessons From 6+ Years of Freelancing

In honor of 10 issues, I thought I’d share 10 lessons I’ve learned from over six years of freelancing for a living.

1. You are more than your job

This is the hardest lesson I’ve learned and one that I’m still actively working on. And I’m sure this is a feeling many of us can relate to, whether you’re a freelancer or not.

It’s easy to tie your identity to your work — especially as a freelancer when you’re the face of your business and in charge of your own income.

But in my experience, tying your identity to your work is a slippery slope that can lead to doubting your worth as a whole. (I wrote about this in the very first issue of Rough Draft).

So here’s a reminder that work is work. If you didn’t land a client, it doesn’t reflect who you are as a person. You are way more than your job!

2. You don’t need a niche

There’s too much pressure for new freelancers to choose a niche and I don’t think that’s the way to go.

Yes, I technically have a niche now but I did a lot of different things when I first started freelancing.

Getting experience in a wide range of marketing and writing helped me figure out what I like, what I’m good at, and what types of clients I want to work with.

(I wrote about this topic in an earlier issue: Finding your freelance niche)

3. Send the DM

One of the questions I hear from freelancers the most is how to get clients.

From my experience, I’ve had the most success with simply reaching out via email or DM. It feels intimidating at first — and I definitely felt like I was going to annoy people on the receiving end — but it’s worked out more times than not.

(Need a little boost of motivation? Here are some examples of real DMs I’ve sent on LinkedIn)

4. Nobody cares (said reassuringly)

Every time I’m about to do something for my freelance business — like post on LinkedIn, reach out to a potential client, or even write this newsletter — there’s a tiny voice in my head that says something along the lines of: “Ewww, don’t do that! Every person you’ve ever met will see this and judge you/hate you/think you’re weird!” 

This thought process is 1) not true and 2) will stop you from putting yourself out there.

The truth is that no one really cares. Everyone is thinking more about themselves than they are of you, which can either be sad or reassuring, depending on how you look at it.

So I guess the lesson here is: Post on LinkedIn even if it feels cringe, start a newsletter if you want, reach out to people you want to connect with.

5. You need a contract

I’m embarrassed to say this, but I didn’t have my own contract for at least the first three years of freelancing.

Some of my clients would provide their own, but when they didn’t, I’d just cross my fingers and hope it all worked out (silly, I know).

It should come as no surprise that I’ve been ghosted, overworked, and not paid all because I didn’t have a contract or communicate my terms. I’ve definitely learned my lesson!

Now, I never start work without a signed proposal or a contract in place.

You don’t need anything fancy, just something that outlines a few terms that are important to you (late payments, rounds of edits you’re willing to offer, etc.).

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6. Trust your gut

You know yourself better than anyone, so trust your gut.

If you get the sense that a client won’t be a good fit after an intro call, then you’re probably right.

If you think a potential project will require more work than usual, then you’re probably right and should raise your rate.

Related: Here’s a handy tool I use to evaluate new opportunities.

7. Remind people what you do

Have you seen those TikToks where people are like “I have no idea what my best friend does for work”?

You may or may not relate to that, but there’s a lesson there: If the people closest to you don’t know what you do for work, then acquaintances in your network probably don’t either!

You have to remind people exactly what you do, especially when you’re looking for more work. Make a post on LinkedIn, or whatever social channel you choose, and remind people what services you offer and what type of client/industry you work with.

And yes, it may feel cringe and uncomfortable but do it anyway (see number 4…).

8. Freelancing can be lonely

I like to work independently, but I think the lack of community caught up with me last year.

As a freelancer, you really have to make an effort to get out of the house, connect with other freelancers, and join communities.

There are a lot of us out there and it’s reassuring to swap stories and bounce ideas of each other.

9. You can just do things

• Pro of being a freelancer: You’re your own boss.

• Con of being a freelancer: You’re your own boss.

Freelancing is both freeing and daunting. You can do whatever you want. You can raise your rates, explore a new service, try to break into a different industry, change the look of your website as many times as you want, start a podcast…truly, anything!

The only person stopping you is you.

10. Take the vacation

Last lesson: Take time off!

Freelancers don’t get paid time off and they also don’t have a boss to encourage them to take vacation days.

There’s also a lot of prep work involved with vacations: Letting clients know you’ll be out, working extra before your trip, scheduling invoices to send while you’re gone…the list goes on.

For me, it feels easier to just work while I’m on vacation (bad habit, I know) or not take time off at all.

But this has led to extreme burn out and is obviously not a sustainable option.

So here’s a reminder to myself and to you: Take a vacation. Spend time away from work. Your work will be here when you get back.

✍️ On a Personal Note

Here’s what I’m up to lately in life, work, and everything in between.

• Doing: I’m running my first 10K this weekend! Any last minute tips from my runner friends??

• Planning: I saw someone on IG say that spring is their New Years and I felt that. I’m starting to get into the groove of the year so I plan on revisiting my goals and getting the ball rolling on some projects I have in mind.

• Reading: For years, I’ve been more of a book collector than a reader (IYKYK) so I’m working through the older books on my shelf before getting any new ones.

I’ll be back in your inboxes on April 15th 💌 In the meantime, let me know what you’re working on and how I can help!

Rough Draft is a bi-weekly newsletter where I share tips and musings on creating a freelance career from scratch. Subscribe here. You can also find me on LinkedIn, Twitter, Threads, or my website. 👋