Sunset In Medellin, Colombia

I Just Lost $6,000+ Every Month

Loren Ross

This is not clickbait that really happened

So What Went Down?

I fired my biggest client, and 10 days later another client left

Poor timing for that other client to leave for sure πŸ˜‚


Flying First Class

A shot from my first class flight over to the US, it might be a while before I’m back in first class


Let’s Start With The Client I Fired

I tried to make it work, I really did

As much as I’d love to continue calling this woman a couple 4 – 5 letter words. At the end of the day she’s not a bad person, she just didn’t have any faith in what I did, and I didn’t have the ability to persuade her.

Was that her fault? Was it my fault? Likely a mix of both.

There was a pretty long period of my marketing career where her monthly payment was equal to my total monthly earnings, so that made it hard to let go.

But my mental health doesn’t have a price tag.

Going Back To My Last Job

A few weeks before I put in my notice at my previous marketing firm, I had a horrible call with a client, someone who was cussing me out and losing his mind on a Zoom call.

When I left that firm marketing firm, I had a vow

1. Work Wherever I Want
2. With Whomever I Want
3. Whenever I Want

PS I left that firm because of a Hawaiian shirt, not because of that client read more about my story here

I’ve had to be somewhat flexible with the 3 goals above, but overall I’ve balanced making money and these goals fairly well.


Quilotoa Lake, Ecuador

A shot from Quilotoa Lake, Ecuador. Ecuador was one of the first places I stayed at long-term after starting my business.


Going Back To The Client From Hell

This woman wanted to know every detail of everything we were doing. It was clear she didn’t trust me at all. She would second guess about half of my decisions, and even flat out say no to strategies we had previously agreed upon.

This not only bruised my ego, I also knew I’d never get a high level of success with her.

Some clients want to find someone to do exactly what they want, then when it doesn’t work it’s your fault, not there’s.

That being said, of all the clients I’ve had in the last 5 years this is only the second one I’ve done this to.

It’s not something I take lightly.

While a healthy life is super important to me, I can’t just give up on every client when we hit a rough patch.

So there are a few things I consider before firing a client.

#1 – I don’t want to optimize myself out of happiness

I’m aware of a part of me that wants to optimize my life into meaninglessness. Where I have plenty of freedom and little struggle. Where obstacles are removed, and each day is easy.

Too easy.

In ridding myself of obstacles, I also lose meaning, excitement, challenge, and the glow of life slowly fades.

I recognize this part of me, so I’m careful of impulsively firing clients simply because I want to make my life “easier”.

#2 – There’s always a chance to learn and grow

I try to take the perspective that the world has no requirement to change, it’s only my perspective that needs to change. That people are generally reasonable, and there’s rarely situations of completely innocent vs. completely wrong.

So I tried man, I tried to do what she wanted. I tried to listen to what she said, I tried to be pliable, but remain firm on the principles of my work.

There are imperfections in every business. Imperfections that your other clients accept, or don’t mention. However, you come across brash clients who proudly pull out their notepads and detail every issue in your business.

But you can only bend so much.


Digital Nomad In Playa Las Galeras, Dominican Republic

A photo of me working from Playa Las Galeras in Dominican Republic. Being able to balance my mental & physical health is the only reason I’ve been able to keep running this business around the world.


For these reasons, I struggled with this decision for the last 2.5 months.

But it just wasn’t working, she continued second guessing everything. Inquiring into every detail, then getting frustrated by the overwhelm that she has no clue how digital marketing works, despite all of her advice.

I dreaded meetings with her, and I left every meeting feeling considerably worse than when I started.

I tried to set boundaries, to put together systems where we can both get what we want, but it didn’t work.

In every nightmare client there are seeds of truth in what they’re saying, and areas for growth.

There are things to learn from clients like this, I realize that I don’t know everything, that my business can improve, that I can do better.

While this is all true, I can not work with clients who don’t trust and respect my perspectives.

You can have doubts, differing opinions, and we can talk about them. But clients who consistently second guess and try to take control of the strategy are nightmares, they ruin my mental health, and ultimately you’ll never get great results.

I didn’t leave my last soulless job to create a soulless business.

Then about 10 days later I got an email

From another client putting in his notice to leave

Son Of A Bitch

While I’ve had tough times in business before, I felt like crying man

I was scared, I felt alone, and most of all I felt powerless.

The same powerlessness I felt when I got arrested in South Africa.

You can fool yourself into believing that you have control over the world.

Life is like floating out at sea on a lifeboat. I can put my boat in order, I can mitigate the likelihood of capsizing, and I can build contingency plans for when the storms come.

However, despite all of the planning at the end of the day I’m at the mercy of fate

Fate doesn’t give a shit what you planned for, or your previous accolades, your daily routine, your mental strength.

It’s neither for you nor against you. It’s doing its own thing, and you are along for the ride.

I recall very poignantly the first time I learned this lesson

On a 12 hour bike ride through the jungles of Guatemala. I was about halfway through my first bikepacking trip. Struggling over a windy, rocky road and envisioning an end at every upcoming turn.

I started screaming and yelling at the “horrible” condition of the road.

I kicked and screamed for a long time that day, until I was beaten into submission.

There’s nothing wrong with this road, it’s a perfectly fine road. It’s my perception that makes it out to be bad.


Cyclist in Antigua Guatemala

A picture of me at the end of this trip in Antigua, Guatemala. If you’re interested in bikepacking – check out my Athens – Instanbul trip here!


This road isn’t trying to hold me back from getting to my destination for that day.

It wasn’t consciously hindering me, or supporting me. It was just a fucking road.

Looking at life through that lense I realize that nearly everyone and everything in the world is the same. They’re neither for me, nor against me. They’re doing their own thing.

I forget this lesson all the time.

In times like this though I am brought back to that remote Guatemalan path.

You don’t have control, and don’t take it personal.


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