This article was published on September 25, 2015

Why I cut my income in half and stopped freelancing

Why I cut my income in half and stopped freelancing
Sean Smith
Story by

Sean Smith

Marketing director & consultant @simpletiger. Marketing director & consultant @simpletiger.

This post originally appeared on the Crew blog.

There’s a lot of stories of freelancing success out there and to most people looking from the outside I could be one of them too.

I’m not going to shy away from the facts here. I’m going to be brutally honest. I’m not gloating. I’ve screwed up more than most. This is simply my story.

I’m not shaming the freelance lifestyle, and I’m not saying ‘everyone should build something bigger’. I’m simply sharing my experiences for those that might be in a similar situation, uncertain about where to go with their career and life.

The realities of a successful freelance career

I was 22, I had just left an agency that I worked at for three years, and I had a roster of on-going clients that afforded me an insanely lavish lifestyle.

I was making ~$110k/year in revenue from freelancing, had just bought a new car, moved into my own place, helped buy my mom a car, and was spending more per-month than I ever could have imagined, all while working from home.

My freelance business was built around marketing consulting with contracts ranging from $1,500–$5,000 a month. Financially, life was good. However, I was dealing with every aspect of running a business. No matter how unstructured or stressful it became I was addicted to seeing how much revenue I could squeeze out of just my time.

It became a personal challenge to see how big I could go and how far I could push myself.

But as I piled on more and more work, I lost sight of the big picture.

I had created so much stress that I couldn’t sleep. I was drinking to dull the headaches and would wake up in the middle of the night to do work because I felt like my clients were going to leave if I didn’t.

The idea of a work/life balance was thrown right out the window.

What is profit if you’re not enjoying it? It’s null and void.

“A man is a success if he gets up in the morning and goes to bed at night and in between does what he wants to do.”–Bob Dylan

The not-so-obvious progression

long road

As the realities of my lifestyle started to dawn on me, I began thinking about one word that seemed like the solution to my situation: scale.

How could I scale my business to create a buffer between me and my work to reduce stress?

I started with the most obvious systems of scale for any freelancer:

  • An easily scalable accounting system
  • An easily scalable project management system
  • An easily scalable onboarding system for clients

As I worked on these, I had another revelation: Why was I setting these systems up for myself, when I could get others to take care of them while I worked on the parts of the business I actually enjoyed?

As someone who wanted complete freedom, and who had just left an agency, starting my own agency didn’t seem like the most electrifying idea. But after some soul searching, I realized it was the right one for me.

My brother (and co-founder of SimpleTiger) Jeremiah and I had already been working somewhat together. We were both freelancing under the same roof, used the same project management system, and even used some of the same contractors for daily operations of our individual clients.

We also both struggled with reaching a breaking point and not being able to escape and decompress.

After a lot of collaboration and introspective talks about what we wanted, what our biggest gripes were about our work, and our goals in life, our decision to create an agency instead of staying freelance seemed pretty obvious.

The ‘why’ is the most important part

In the end, there were three main reasons that pushed us to give up our freelance careers and build an agency:

1. We wanted to stop worrying about the money

This may sound ridiculous when you think about the fact that I was making $110k/year freelancing, but the issue was that the money became the sole reason for my career choices. By creating something bigger than ourselves, we created distance between ourselves and the finances, automating the expenses, and allowing ourselves to focus on our work and on the people we work with and for.

2. We wanted accountability

You only push just hard enough when you’re only accountable to yourself, we wanted to push harder, to go farther. Not all of us have the willpower to constantly go, and go, and go. As individuals, we all succumb to burnout at some point. By bringing in other people, we became driven to provide them with a better life.

The motivation moved away from being purely selfish and is now a source of energy for when we’re feeling drained.

3. We wanted to build something bigger than us

Jeremiah and I are both keenly aware of our strengths and weaknesses. As freelancers, those weaknesses became a constant source of stress. By building something bigger, we’ve been able to bring in people who are skilled in areas we aren’t, and give them the autonomy to shape that part of the company.

We want to go further, not faster.

Knowing myself and my brother, if we had stayed freelancers things would have changed. We probably would have accepted positions that we weren’t as free in simply because it was easier and less stressful than being a lonewolf.

With our agency, we get to steer the ship, we get to decide how fast we move, and how fast we grow.

Creating a company is like creating a marriage, you’re committing to a future together. What it brings, if you’re willing to make the commitment, is security, structure, teamwork, love, and accountability. These are all principles that we intrinsically need to keep linked to our work.

I’m not saying you can’t get these in a freelance environment, they were just hard for us to find while being stuck in the weeds.

The caveat: It isn’t all green

There are always risks, and the dips seem even more stressful now than before because we have other people we’re responsible for. However, this stress has become a source of motivation, rather than being a weight on our shoulders.

Businesses fail every day, and it’s always a prospect that will be seeded in the back of our minds. But what do we say to the god of failure? ‘Not today’.

Ultimately the buck still stops with you—you’re the owner, you bear the responsibility, but the structure you set up opens up a less stressful outlook and lets you focus on what really matters.

Here are a few of the things that immediately changed when my brother and I combined our work and became co-owners of a single agency:

We cut our incomes in half. This was to account for the new hires and to keep resources open to invest in the growth of the company quickly. I went to a $65,000/year salary, with bonus incentives.

We gave up certain responsibilities. I now focus almost entirely on strategy, content, and social, as well as bringing in new clients. Jeremiah focuses on analytics and technical, as well as also bringing in new clients and general administration. We both play to our strengths and relinquished responsibility of what we aren’t naturally talented at.

We had to train others. Bringing on new people means you need everyone on the same page, especially if you’re a distributed team like we are. Early on, we spent time defining how we wanted things to be done, including training courses and incentives for anyone bringing in new business.


The pleasant side effect of all this is that with less administrative stress placed on us we can focus in on doing meaningful work. We’ve even been able to increase our average income per client by showing the increased output in performance.

In the end, our process has created a cycle of better work > happier clients > more income.

What to consider when you quit freelancing

I have plenty of friends who are exclusively freelance and love it.

I also have plenty of friends who were freelancers that specifically built businesses for the freelance community to help other freelancers as a way of no longer needing to be on a consistent grind.

People like Paul Jarvis (who created, and Robert Williams (who created, even the team here at Crew who built their company around helping individual freelancers and agencies find work.

There are so many different solutions out there that aren’t part of the traditional working world and what works for you will depend on how you answer these questions:

  1. What are your biggest gripes about what you’re currently doing?
  2. What are your biggest strengths in what you’re doing and how could you leverage those strengths to make things easier and reduce the effects of the gripes in #1?
  3. Is staying freelance really your best bet? Or should you take steps towards creating a product, agency, or something that goes beyond just yourself that you can scale to take on a life beyond your freelancing grind?

I definitely made more money freelancing and could probably make more personally now than I ever did if I wanted to, but currently I’m just excited by the changes we’re making—changes I wouldn’t have been able to make had I stayed focused on my own money and selfish pursuits, instead of focusing on what good I could create for others, together.

To each their own, and as always:

“Adapt what is useful, discard what is not, add what is uniquely your own.”–Bruce Lee 

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