The Crossroads Between Security And Freedom

In April, I started my leap. For 6 months I would be on leave from my 9-5 job to try to take my business full-time. The goal was always to turn my creative business from a small side business, to something I could keep doing full-time. But I knew there was a big chance I wouldn’t get all the way in 6 months time.

At the end of summer, a little over a month left of my 6 months, I knew I had to choose. Would I go back to my job, maybe fewer days a week, or would I keep going full-time? Neither option was perfect, and I found myself at a crossroads between security and freedom.

End of leap worries

Here’s how things had been going in the business up until that point. April-May: great. June-August: not so great. In the beginning of my leap, I was filled with energy and inspiration, people responded well and I booked in coaching clients, more at once than I ever had before. At this point, I felt optimistic. Then I attempted a summer campaign that mostly flopped, I hit the messy middle with all sorts of mindset challenges, then I slowed down for a summer break, everyone else slowed down and things became very… still.

I had expected summer to be slower, but hadn’t expected the change to be so drastic. I tried to hold my nerve and not worry. At first that attempt went well, but as I started to ease back into work in August I got more and more worried. Maybe it wasn’t just the effect of summer. Maybe those two months in spring when things went well were just a fluke, created by the excitement I’d managed to build up around taking my leap.

And then a lot things happened at once.

  1. A colleague from my job reached out to suggest maybe I could come back part time to do communication work, which was the part of my 9-5 job that I had enjoyed the most. My job let me know they needed to know soon if I would be coming back in October or not. I replied suggesting that I could come back two days a week to do communications work. They said they would discuss it internally.

  2. A magazine contacted me about an article pitch I had sent out (and given up on), and said they wanted to publish it. Another brand contacted me to ask if I wanted to write a guest article for them. Other little things started popping into my inbox.

  3. I convinced myself to hold a live workshop, which I had been a little frightened of ever since I did one 4 years ago and only one person showed up. I wanted to test out a group offering, so I created the free workshop Back To Creativity. I half-jokingly set the target of getting 50 people to sign up, not thinking I’d reach it. 70 people signed up. After three mostly quiet months, I booked three coaching clients in three weeks.

Clearly, autumn had begun.

We’re trained to avoid risk

I’ve never been a risk-taker. I was quiet, got good grades, picked the secure education over the creative one, became a government bureaucrat. That’s what society tends to push us towards. School lays out the path to follow, media paints the picture of a dangerous world. We’re trained to look over our shoulders, to get the secure jobs, to stay put and stay safe.

I’m not saying there’s anything wrong with avoiding risks. But when our fundamental approach to the world is to never take risks, we also avoid things that can bring us happiness. Starting relationships, moving to a new city, making career changes, pursuing creative projects… they all involve an element of risk. The risk of getting hurt, of disappointment, of failure.

These past 6 months, I’ve realised just how deeply that risk avoidance has been instilled in me. When choosing to do something I want despite risk, I feel like I’m doing something wrong. Even if I’m okay with the risk, it feels like I’m breaking the rules.

But I’ve also realised just how much freedom means to me.

Choosing freedom

It’s not a coincidence that I thrived at university studying political science. With only a couple of hours of scheduled time per week, I could plan my days, pursue my ideas and live life pretty much how I wanted. I highly considered getting a PhD, but opted not to because I longed to work in society, not only study it.

That freedom was lost when I started working 9-5. Suddenly, I was a tiny cog in a giant, stale system. I was expected to sit at my desk for a certain number of hours, regardless of how I worked best. The work I did was a result of a steep hierarchy, completely beyond my influence. My days were further controlled by check lists, routine descriptions, policies and documentation. This, the whole system… I hated working within it. Even if I have enjoyed parts of my job, and had great colleagues, I despised this way of working from the very core of my being.

So when my boss said “no, you can’t come back two days a week to work with communications. You can come back and do what you did before, and we can maybe allow you to work a bit less.” Then the overwhelming feeling was relief.

I didn’t want to go back. The sweetened option of coming back part time to do what I had enjoyed most at my job… the security had been tempting, but I never really wanted that either. I wanted to choose freedom, despite the risk. So I gathered my courage, and I quit my job.

A note here on privilege is needed. I have savings, savings I haven’t dipped into as much as I thought I would these past 6 months. I have a partner who pays a bigger share of the bills as I’m building my business. Had I been single and without savings, I likely would have made another choice. I probably wouldn’t have been able to do my 6 month leap to begin with.

The point isn’t that everyone should quit their jobs and take all the risks. It’s that even when the risks aren’t that big, they can feel huge. And that feeling can stop us from living life the way we truly want.

Freedom means both gaining and letting go of control

To choose the path of freedom means you’re taking back control. I’ve taken back the control over how I spend my days, what work I do, how I live my life. That feels amazing. But freedom also means you have to let go of control.

Security is predictable. You know which day the pay check is coming and how much it amounts to. You know what you’re expected to do, what will happen if you do it. There’s comfort in this, of course there is.

Beyond security, more things are outside of your control. I don’t know who my next client will be or when they’ll book. I don’t know how fast my business will grow. I don’t know if my group offerings will be popular, if my campaigns will work, whether I’ll be a business owner for the rest of my working life… or not.

This has felt uncomfortable. After so many years on the secure path, it has felt scary to not know. But guess what? I’m starting to get used to it. Dare I say, enjoy it.

In the unknown lies possibilities. It’s the land of creativity, growth and freedom. In the crossroads between security and freedom, I’ve chosen the latter.

I’m keeping going full-time with my creative business. It’s still early days, my income is very modest, things are up and down and I’m learning so much. But I’m returning to my word of the year: trust. This choice is one of trust, of trusting myself. That I’ll keep figuring things out.

Actually, it’s probably the most I’ve ever trusted myself.


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Six Ways My 6 Month Business Leap Changed Me