I Left My Job To Freelance During COVID: here's what gave me strength

Yesterday, I was an employee at a well-respected software consultancy.  Today, I’m completely alone in my office, and there’s nothing but silence.

Yet, I feel completely at peace with this moment, and gracious that I have the opportunity to embark on my life’s work.

Today I want to share with you four strategies that I used to overcome my fears of income, loneliness, and failure.

Starting with a single customer

One of the major problems with freelancing is that it takes about a year to build up a consistent client stream: and “no clients” means “no income”.  I solved the financial portion of this problem my living frugally, saving money, and doing expensive automotive and home repairs myself.

However, an ice-cold fear still gripped me:

What if I can’t find any clients???

In my case, this fear was particularly difficult to overcome, because I didn’t have time to freelance “on the side” while maintaining a family, a full-time job, and a household—that would have meant starting out as a freelancer with zero income, which would have been terrible for my mental health, forcing me into a scarcity mindset from the get-go.

To mitigate this fear, I kept my eyes and ears open for a full year, prior to leaving my job, searching for a tiny 5hr/week project, that I knew I could maintain while working full time.

When I embarked on my full-time freelance journey this morning, I started with an existing client relationship, and an existing income stream.

Even though the financial impact of this project was small, the benefit to my emotional health was huge.

A strong daily routine

In some ways, the age of COVID was very good to me.  I was able to work from home, which improved my productivity quite a bit.  More importantly, without the confines of the office or the daily two-way commute, I was able to set up a rigid daily routine of spiritual work, exercise, and writing software.

As time went on, I became very aware of my daily rhythm: when I was alert, when I was hungry, and when I was tired and unproductive.

I engineered my work day to revolve around my personal rhythms, and created a strict schedule that I could adhere to every day, and find success.

This morning, I woke up at the same exact time that I always have, turning on my computer, and began working, exactly within the same strict schedule where I’ve found comfort and success over the last year.

An awareness of the fleeting-ness of life

When COVID hit, it nearly stalled my freelance journey, because I feared different bad scenarios and consequences that could happen in the future:

• what if my family developed COVID; would my new ACA healthcare plan cover those costs?
• what if, after leaving my current company, I found myself alone and outcasted from the local dev community?
• what if my home needed a major repair, and I couldn’t cover the costs?

These fears were partially solved by creating contingency plans and strategies for handling the situations, should they arise.

However, the final bit of strength to overcome these fears came from a strange place:

Even before the COVID lockdown began, I made it a point to go on a daily walk.  During these walks, I encountered homeless people sleeping in the park, car accidents, and dried leaves being crunched under my feet.

During these moments, I would wonder about those people involved in the car accident, and how there was nothing they could have done to prevent that from happening.  Or I’d pass homeless people, imagining the situations they were born into, that they had no control over, and wondering if they'd ever find a way out of their suffering.

Simply being aware of the big-ness of the world, and the different cards that Fate could deal a person at any time, outside of human control, was enough to place my fears into their correct perspective—trifles, in the grand scheme of things.

A list of the good situations you’re leaving behind, and what created them

I’ve saved the best source of strength for last—spoiler alert: it’s another awareness, an act of consciousness that you can practice and improve over time.

Whenever I’ve contemplated leaving different jobs in the past, I always found myself gripped by an icy-cold fear: “Whoa, I have it pretty good here, am I really sure that I want to leave?  What if these good times never return?” This fear is compounded when I witness scores of people that I’m surrounded by, suffering in different ways, in their different jobs and situations that they find themselves in.

During these moments of fear, I’d list out all the ways that I was “winning” at my current job, and how I was so grateful and thankful at the fact that these opportunities existed at all:

You have it too good here; don’t go

But then I examined each of these situations, and asked myself, “What created the situation to begin with?”.  In all cases, I found that the good things in my life were created by two things:

• various external opportunities that I couldn’t control
• an internal decision to excel at whatever I was doing, which I could control

That second item was the key.  After walking through these various situations in my mind, I realized they were created by my internal essence expressing itself, not by the situation themselves, which come and go.

After making this list, I realized that the good times were created when I allowed my enthusiasm to through me and into my work, and therefore anything I could do to cultivate that enthusiasm would lead to a positive outcome.

And now here I am, doing my life’s work, and writing this blog post.

Good luck on your own freelancing journey, if you are considering it, and I hope these places where I've found strength will also help you on your own journey.