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Everything You Need to Know to Succeed as a Freelancer

tanoaksam profile image Sam Tanoak Sycamore Originally published at blog.sycamore.design Updated on ・6 min read

First off: who am I to be offering this advice?

  • I've been freelancing off-and-on as a writer since 2012
  • I have been self-employed or at least side-hustling for most of my adult life
  • I currently freelance as a web developer and technical writer for agencies and tech startups

If you follow me on Twitter, you're probably most interested in how to get started as a freelance web developer.

If you're interested in getting paid to write, a lot of my advice will apply to you, too.

1. You Need a Vertical

When someone asks about your taste in music, the worst answer you can give is "I like a little bit of everything."

OK, but- what are you actually passionate about?

The same goes for freelancing!

Your "vertical" is the market or industry that you target.

You need to be very specific about who you serve, and what you offer.

I got my start in freelancing as a music journalist. I wrote about specific genres of music, and established a name for myself as a vocal supporter of my local music scene.

I was "that local music guy."

Now that I'm in tech, people know me as "that tree-hugging dude who's into the Jamstack."

You need to be able to sum up your personal brand similarly.

Speaking of which...

2. You Need a Personal Brand

I know. It sounds gross. It grossed me out for way longer than it should have.

But look- if you interact with other people in public, guess what?

You have a personal brand.

And if you're intentional about crafting that brand, you can establish yourself as an authority on the services you offer within your vertical.

This is another instance where it really pays off to "niche down."

The more specific your niche is, the easier it will be for you to make yourself known as the go-to person within that niche.

How do you become the go-to person for anything?

3. You Need to Network

This was another one that I was allergic to in my younger years, and I just ended up shooting myself in the foot over the long run.

Establishing professional connections doesn't have to feel weird or phony.

It's only disingenuous if you decide to be disingenuous about the relationships that you cultivate!

The people you want to network with know how this game is played.

They aren't going to think it's weird if you DM with a question or ask to have a chat.

That's how we forge these relationships.

Twitter is where the vast majority of my networking takes place.

It's truly incredible the kinds of relationships you can build purely by sharing what you do.

If you want to know more about how I tackled networking when I was brand new to the tech industry, check out my piece here:

My Networking Strategy for Making Meaningful Connections in Tech

4. You Need Clients

Well, duh. Easier said than done, right?

How the heck do you land that first client when you don't have any experience, nor much of a professional network?

The short answer is:

Be very vocal about the services you offer!

Your first client could easily be a family member, a friend of a friend, that dude from college you're still friends with on Facebook...

Start with your personal network. You don't have to treat it like multi-level marketing or anything.

Just make it known what you're up to and what you can do.

You never know who might know somebody who knows somebody who might want to hire you.

If that doesn't work for you, another approach is cold-emailing.

I had some success at this when I was just getting started.

That said: it's a numbers game. It can be very tedious work, and a full-time commitment just to find prospective leads.

The vast majority of emails you send will be ignored.

For every 100 carefully targeted, meticulously curated emails you send, you might expect to close 1 or 2 deals if you're lucky.

Nobody said it was easy.

If you want to know more about how I did it, you can read about my workflow here:

My Freelancing Workflow, From Cold Leads to Paid Invoices

5. You Need Patience and Diligence

I don't care how talented you are - this isn't going to happen overnight.

The only way this is going to work over the long-term is if you are diligent about establishing your reputation.

People who casually follow me on Twitter know me as a freelancer in the tech industry - that wasn't an accident!!

I put in the work over time, and it has paid off.

Essentially all of my marketing happens on Twitter now.

People approach me with work now - sometimes more than I can take on.

All because I have been intentional about how I present my personal brand to the world.

6. You Need to Upsell

Who are the people you should be targeting the most with your marketing?

The people who are already paying you!

The simplest way to land more work is to make it known to your existing clients that you can be hired for additional work.

See something that needs doing? Write a proposal outlining how you would do it, and why it matters!

Ask - directly - for referrals!

There's a good chance your clients know other people who might want to hire you.

But most people aren't going to go out of their way to make those connections on your behalf.

Unless you ask.

7. You Need Multiple Revenue Streams

My career as a music journalist imploded in 2014 when my one long-term client suddenly shut down and I couldn't sustain myself off of free concert tickets alone.

I put all of my eggs in one basket, and didn't prioritize forging stronger relationships with other potential clients while I was so comfortable with the one.

When you're self-employed, nobody owes you a paycheck just for showing up.

When the contract is fulfilled - or otherwise can't be renewed - you're on your own.

Your networking and marketing efforts can't stop simply because the work is flowing steadily today.

Even if you have one or two big clients paying your bills at the moment, you should always be diligent about forging new relationships and strengthening older ones.

You never know where your next big deal might come from.

Also- consider ways you might be able to "productize" your services.

If you're a subject matter expert, you might write a book or launch a course.

If you have a particular service with a process that looks pretty much the same for all clients - like an SEO audit or a content strategy consultation - you could turn this into a flat-rate product rather than charging an hourly fee.

I'm not a fan of the term "passive income" - the work it takes upfront is anything but passive.

That said - it never hurts to have some extra cash show up on a regular basis for work you completed months or years ago.

8. You Need Tools to Make Your Life Easier

I don't know what I would do without Freshbooks for accounting and invoicing.

For digital contracts you can use HelloSign or DocuSign - I've found them to be pretty much the same on the free tier.

All of my research, note-taking, and writing happens in Obsidian. There are many other options out there for this kind of thing, but I'm happy with my decision.

You will probably want to set yourself up with Google Workspace for a custom domain email, and Search Console to keep track of analytics on your portfolio site.

(You do have a portfolio site, right?)

Finally, consider ways to manage and track your time.

Calendly is a fantastic tool for streamlining the process of scheduling meetings.

I'm a big fan of the Pomodoro method for time management, which involves setting a timer for 25 minutes of focused work, followed by a 5 minute break.

This is how I structure my daily schedule and keep track of how much time I invest in any given project.


If you enjoyed this piece and you want to keep up with my work, you can sign up for my email newsletter through this link. I promise to make every email something you will be excited to open!

Discussion (2)

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mccurcio profile image
Matt Curcio

Hey Sam,

  1. I love Santa Cruz. I have family there, within ear-shot of the yells from the roller-coaster. lol.
  2. I really like the layout for the web version of your cv. Very clean and tidy.
  3. I really really like the formatting of this article. I like the formatting maybe because I find black text on a blank white screen almost too busy. Makes it much easier to read. Just clicks with me.
  4. Finally, I like your approach to setting up a client list and branding. You seem to say it doesn't have to be a chore if you like it and you are not insincere about it. Thanks
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tanoaksam profile image
Sam Tanoak Sycamore Author

Thanks Matt, I appreciate all the good vibes!

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