The Most Important Stoic Lesson for Freelancers

It’s a bit of a cliche in the world of entrepreneurs and Silicon Valley but it’s true – there is a great deal that we freelancers of 2022 can learn from the ancient Stoics. 

Any kind of wisdom that has survived a gulf of 2,000 years is usually worth listening to. It has been passed through the the generations and centuries to the present day for a reason. 

Related: Mindset Matters – How to Build the Rock-Solid Freelance Mindset You Need for Success
stoic lesson for freelancers: blog article by Freelance Success

Here’s one of my favourite stoic lessons for freelancers.

I’ve found it particularly helpful during the more challenging moments. Times when my career has seemed to be at a dead-end, times when I’ve had too much work on my plate or times when I’ve felt unsure about what I should do next. 

It’s summarised by Ryan Holiday in his highly accessible intro to the ideas of Stoicism, The Obstacle is the Way:

“There is always a countermove, always an escape or a way through, so there is no reason to get worked up.”

Ryan Holiday

This is a deeply simple stoic lesson, but it’s so easy to forget it when you’re flailing around in the middle of what seems like a huge crisis.

It brings together the ideas of defiance and acceptance, which can be so helpful in navigating your way through difficult patches.

When everything seems to be going wrong, or falling apart, looking for your countermove can make all of the difference.

The truth is, we often exaggerate our problems, or waste time ruminating on them without any intention to make a change or take action. This is human nature, but it’s torturing yourself for no reason.

I think the most important stoic lesson comes from Seneca in this simple but profound quote:

“We are more often frightened than hurt; and we suffer more from imagination than from reality.”


The lesson here is simply to try and worry less about things that don’t need worrying about. Challenges often seem overwhelming and intimidating in your mind – so it’s important to try and find perspective when you can. The Stoics teach that troubles and obstacles are to be expected on your journey. Nobody promised you it would be easy.

Adopting this Stoic approach takes practice, but the more you can remind yourself of this lesson, the more you will start to see that problems do not need to cause you to suffer more than necessary.

So by framing your response to accept the challenge and then carry on anyway, you’re cultivating a mindset that will help you to keep going strong, no matter what challenges you face.

We know that growth and progress comes from overcoming challenges and coming out of the other side. So in a way, we can be grateful for the challenges that we face in our career, knowing that they are helping us to grow, learn and adapt.

Now, of course, it’s difficult to remember lessons like this when things are tough, but the ideas of the Stoics can really help modern-day freelancers to keep things in proportion and react in constructive ways.

If any of this has struck a chord with you, I really recommend diving into some of the resources below.

More resources about stoicism for modern days:

If you want to dive deeper into stoicism, here are some resources we recommend to get started:

If you like this article, you might like these as well:

Is the Voice in Your Head Holding You Back?
Setting New Year’s Anti-Resolutions
A Simple Hack that Makes Decision Making Easy

Until next time,

Alistair signature