Master freelancing by building your exit plan 🚀

Howdy!

A lot of people here are either looking to begin freelancing or are full-time freelancers.

And it makes sense. 

Freelancing is often the easiest path to building a location-independent lifestyle. 

I’ve been wanting to dedicate a whole newsletter to freelancing—covering its nuances, preparation, and strategies for maintaining top-tier clients. In other words, the granddaddiest of granddaddy guides on freelancing. 

And that’s why I’m so excited to introduce you to my friend, Nick Lafferty.

I first met Nick back in 2015 when we were both tethered to desks at a startup in Austin, Texas. Nick has since gone on to work for fast-growing startups like Loom, before quitting his job in May 2023 to start a growth marketing consulting practice. Six months later he was earning over $30k/month in revenue. 

He also started a newsletter called the Early Exit Club where he transparently shares everything about his freelancing journey: how much revenue he makes every month, how to find freelance clients, and how much to charge them. 

Now I’m picky when it comes to newsletters. And Nick’s is one I look forward to reading every week. So when he said he’d be down to share his freelancing framework with us SiteSeers, I was stoked.

Without further ado, let’s dive into the freelancing world with Nick.

Hey, this is Kelsey, and you’re reading the SiteSee newsletter. Think of me as your Big Sis when it comes to travel, inspiring you to keep going places. You can expect an email from me every Friday filled with nomad stories, tips for living a location-independent lifestyle, and the gear to get you there.

Travel Story: Stop Playing It Safe

In May 2023 I quit a job making $180,000/yr at a well-funded startup to work for myself.

While no job is truly ever “safe”, that job felt about as safe as it got during a year where over 200,000 people were laid off.

I felt crazy for quitting, but now 10 months later I only have one regret.

Not doing it sooner.

I crossed $30k/month in self-employment income 6 months after quitting my job, made from a mix of freelancing, affiliate income, and banner ads on my website.

This is a story about me, but more importantly, this is also a story about how you can do the same thing. But only if you stop playing it safe.

Rewinding the clock

I’ve spent almost 10 years helping software companies like Loom grow with paid ads, SEO, and affiliate marketing, but as I moved further in my career, my tenure at each company became shorter:

• 1st job (2014-2019): 4.5 years

• 2nd job (2019-2021): 2.3 years

• 3rd job (2021-2023): 1.7 years

• 4th job (2023-2023): 5 months

I spent much of that time chasing the elusive Director title and never actually getting it. In hindsight, I now realize that was completely the wrong goal.

I was working towards a goal that didn’t actually matter. Only after I sat down and reflected on what I wanted from life (not just a career), did I figure out what mattered to me.

But those 10 years taught me everything I needed to successfully work for myself and gave me the professional network to back it up.

I finally had to just rip the bandaid off and go. It was now or never.

Finding the right time to quit

I created a four-step framework to help build conviction in my decision to quit a job during the worst downtown the tech industry has ever seen. It looked like this:

1. Define your ultimate goal

2. Track your monthly expenses

3. Find short-time income

4. Build an emergency fund

Only once I had checked all these boxes was I comfortable taking a leap of faith. Here’s how I look at each of those four steps and why they were important to me.

1. Define your ultimate goal

There are a million reasons to quit a job, but it was important for me to quit towards my passions instead of quitting away from my problems.

It’s fine to be motivated to leave a shitty job, but you need to quit towards something that fires you up because without that motivation, it’s much harder to succeed.

So how do you define your ultimate goal? Here’s the thing: it’s entirely up to you!

• Do you want to be location-independent?

• Do you want to spend every Friday with your kids instead of sitting in meetings?

• Do you want to take every summer off to spend with your partner?

Any and all of those things are possible. Figure out what matters most to you and build a freelancing business around that.

Here’s my goal: I want to stop having to work by the time I turn 40.

I just turned 35, so I have exactly 5 years to get there.

After I turn 40 I want to be highly selective of the work I do from that point on, which means I need to be financially successful now to set myself up for a more comfortable life post-40.

I have a higher likelihood of reaching that goal by working for myself, where my income is uncapped.

I don’t need to fight my boss or the HR team to give me a raise, I just find another client or raise my rates.

2. Track your monthly expenses

Understanding how much you spend in a month is so important. Because without knowing your expenses it’s impossible to build an emergency fund that can last you 3-6+ months if things don’t go according to plan.

And trust me, things will not go 100% according to plan.

My HVAC broke 2 weeks after I quit my job, creating an instant $3,000 repair bill. It was the worst possible timing, but I was fine. We had savings to cover it.

Use budgeting software like YNAB or Tiller to review your expenses over a 3-month period.

Why 3 months? That’ll help give you an average that accounts for all the curveballs life throws our way.

You’ll also find some areas that you can likely trim down to extend your financial runway. Knowing what levers you can pull is important when you’re going off on your own.

3. Find short-term income

The biggest mistake I made early on as a full-time freelancer was saying yes to every single opportunity that came my way.

Red flags from a client? Conveniently ignored in favor of a paycheck.

Soul sucking work? Painfully dragged through to get more dollars in my bank account.

Then I got smart and started heavily filtering my clients based on the type of work that gave me joy or not.

The filter I used was my personal positioning statement which starts by defining exactly the type of work I do and for who. A couple of tips:

• Spend time to nail your offer as a consultant: You should be really crisp on answering the question, "What do you do?". Here’s mine:

  • I’m a growth marketing consultant for B2b SaaS companies from Series A to Series C who helps plan and execute authority-driven marketing campaigns via Google Ads and LinkedIn ads to build sustainable sources of revenue growth. I work best with founders who understand the value of organic social and who enjoy posting regularly on LinkedIn.

• Reach out to former colleagues / managers / VPs that you worked with in the past: Tell them your offer and ask if they know anyone who needs your help. Skip freelance marketplaces like Fiverr and UpWork and instead tap into your network. Every single person you’ve worked with can be a great source of referral work for you, but you have to ask.

I’m also a big advocate of posting on LinkedIn because it’s built the foundation of both my freelancing business and my personal newsletter.

Talk about your life and work experiences. Share stories of vulnerability, times you’ve royally screwed up, and things you’ve learned along the way.

Do this for long enough and you’ll start to gain followers. Those followers will tell other people about you, and those other people might need your help.

4. Build an emergency fund

I had 6+ months of expenses saved before I quit my job. My wife also works for herself, so both of us going freelance was a greater risk.

Neither of us had access to health care through our jobs.

I wanted to be absolutely sure we could cover any emergencies that came up without stressing about it. And having a big chunk of cash in the bank (earning a 5% interest rate in a high-yield savings account) helped put my mind at ease.

Please, do not skip this step.

The next five years belong to me

I have never felt more in control of my life, both personally and professionally, than I do right now.

I have a mix of freelancing clients that fit into my personal positioning statement and they’re really fun to work with.

I set my rates. I set my working hours. I set my vacation time.

While this is a double-edged sword, the freedom is refreshing compared to the last 5 years of my career.

And I’m finally excited to work. I’m doing exactly the kind of work I want to while having far fewer meetings and corporate BS to deal with.

This path isn’t for everyone, but it’s my mission to help anyone who thinks this is the life for them.

I started my newsletter, the Early Exit Club, to share my story and inspire others to take a similar leap of faith. If you enjoyed this then I hope you’ll follow along and send me an email with your story.

— Nick Lafferty

If you want to connect with Nick, you can follow him on LinkedIn here, or sign up to the Early Exit Club Newsletter here.

Gear Check🧳

There are three things you use every day and should justify spending more money on. This includes: 1) A high-quality water bottle (YETI is my preferred choice). 2) Sunglasses that you adore (Ray-Ban is my top pick). And 3) a hat offering excellent protection.

I've been grieving over the loss of my bucket hat, which I left at a market a year ago. However, my closest friend introduced me to this bucket hat from Lululemon. While I usually prefer supporting smaller, sustainable brands, their hat is top-notch, and I feel compelled to recommend it. Crafted from a lightweight fabric with sweat-wicking and quick-drying technology (translation: it's machine-washable), this bucket hat is a must-have if you're in search of a new one.

Airport Reads🗞️

• This post on X which one commenter said “should be taught to every person in high school and college.”

• Dreaming of finding your ikigai, or just having some bangin’ sushi? Japan announced a 6-month digital nomad visa launching this spring.

• Hot girl walks are out. “Soft hiking” is in. This account shows you what it’s all about.

Last Thing✨

Over the last week, my best friend and his partner came all the way out to South Africa to visit. 

It’s been a poignant reminder of the very reason I embarked on creating a location-independent lifestyle in the first place: to cherish the freedom of being with the people I love doing the things I love, and doing so on my own terms.

Have a wonderful weekend, I’ll see you here next week!

Onwards,

Kelsey

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