If one of your career priorities is financial security, traditional employment may no longer be your best option. Nathan Ryan believes becoming a freelancer can make your career more resilient by forcing you to become more adaptable.

He’s somewhat of an expert. He’s had several different freelance seasons of his own throughout this career.

He recently pivoted back into freelancing when he gave up his role as a CEO of an agency. Currently, he’s the co-founder of a design thinking consulting practice called Blue Sky Partners to help business put systems in place, so they can scale.

Lot of great lessons in our conversation including:

How Nathan defines freelancing and how it’s changed over time.
Pivoting from running an agency to becoming a freelancer again.
How curiosity helps you deal with uncertainty.
Setting a monthly income goal as you transition into freelancing.
Disconnecting the value of your work from the time you spend doing it.
Using design thinking to maximize time.

Life Skills That Matter In This Episode

Reframe your mindset
Plan your actions
Embrace discomfort
Build your community

How Nathan Works and Thinks

Wake up time: 5:15 am
Core work activities + habits: 1) Attending events. 2) Following up with new contacts. 3) Meeting with his business partners.
Ideal work environment: Early in the morning in his home office with some kind of ambient/techno music blaring.
Definition of success: The opportunity to work with the people he wants to work with, on the things he wants to work on.
Regains focus by: A workout or a walk.
Favorite productivity tool: Basecamp and Field Notes notebooks.
90-day goal: Do 3-5 of their new workshops and immersions per month and have 5 clients at 6-month contracts.

Inspirational Quotes

“If you really understand what is being automated, then automation is going to be helpful.”

“I always had friends around and was always able to find a community where everybody else was pushing themselves in the same way that I wanted to be pushing myself.”

Coaching Advice

If you’ve been thinking about freelancing or you’re ready to try it for yourself, Nathan recommends these first couple actions as a way to get started:

1) Get really tactile and understand how much money you need to live comfortably and then work backward to build your pricing and unit structure.

2) Give yourself between 3-6 months of runway before full making the jump.