The journey to freelancing confidence

CB065487This is the second in a series of three posts on quitting paid employment and reinventing your life and work. It’s based on my own experience of having exited a so-called top job twelve years ago, and having subsequently made a good living from doing what I love.

One of the things I really struggled with was the whole emotional roller-coaster ride. One day I could be thrilled at the prospect of running my own show. The next, my stomach would be in my mouth as the terror of being entirely dependent on myself for making a living hit me. Often, I wished that I could just stop feeling – that way I’d make the change with a whole lot less grief.

As it transpires, I discovered that the emotional ride was actually a fairly natural and necessary part of the process. Here’s how I found my way through the minefield of feelings and got to the other end successfully.

Preparing to leave

  1. Excitement. Quite apart from any negative feelings that my paid job was engendering at the time, what drove me on was the elation I felt at the thought of doing my own thing. I imagined how wonderful it would be to work in a way that was more self-directed. And especially after I did work to envision my future life, I could touch and feel how much more energy and zest I would have. How much more freedom I would have to pursue things beyond the bind of the corporate career.
  2. Doubt, fear and anxiety. But as I got further into thinking and planning what I wanted to do, some yuckier thoughts and feelings emerged. “People will think I’m crazy,” I said to myself. “What could I sell?” “I’m not really good enough to go it alone.” Looking back, I notice how often I slowed myself down with this kind of thing.
  3. Anger and frustration. Eventually I got pissed off with how long it was taking me to do something decisive, and, indeed for thinking badly of myself. This, coming at a time when my job was on its last legs, brought me to a point where I felt compelled to act, decided to resign, and did.

Ship to shore

  1. Relief. From the moment I resigned, the worrying was over. I had set sail and there was no going back. From the months of wondering about whether or not I’d be able to make a go of it myself, I was suddenly in the position of having to put myself to the test and I had a fresh burst of focus and energy. I stopped caring about what anyone else thought.
  2. Disorientation. Post the leaving party, things felt rocky for a while. Going from working with large teams around me, and having the enviable technological and administrative support of big corporations, to being entirely self-sufficient was initially quite disconcerting. It was now entirely up to me to set my own goals and review my performance. There were no landmarks like weekly team meetings or client reviews that charted the map of the week. There were times when I lost track of what day it was. All my known reference points were gone. I had to set my own structures and support systems and they had to work for me. In the beginning that was hard. I’d work late into the evening to set things up on my computer or to master computer software that I’d previously only had a passing interest in.
  3. Incompetence. The other huge surprise was that I initially lost the feeling of seasoned confidence in my work that I’d built up over my years in corporate life. Suddenly I was doing things in a completely different way. I was having to learn different skills – like invoicing, accounting. Even the form of selling I was doing was quite different from what I’d done previously. This added to my wobbliness.
    It took me to some time to realise that, although I was creating what I’d believed I’d wanted, this was entirely new territory to me, and I was going to have to acclimate to it like the Pilgrim Fathers had to when they set foot in America. Giving myself permission to be that newcomer allowed me to slow down, ease the tension I was feeling, and take things a day at a time.

Happy landings

  1. Confidence. After months of living and working in what felt like foreign territory, the world started to look and feel better. “I can do this!!” I started to think. This in turn made me feel surer of my footing and stronger in what I did. Meaning, my results improved, I got great feedback, and I felt fantastic.
  2. Certainty. “I’ve done the right thing,” I started to tell myself as I began to sense solid land beneath my feet again and to feel more at home.
  3. Joy and happiness. The bliss of doing my own thing is now immense. I won’t pretend that there aren’t times when I feel challenged by things I confront in the process of doing my work and living my life. Or that the type of work I do has stayed the same in all the years I’ve worked for myself. But there were some significant lessons I learned from making this journey that I now apply in an ongoing way to my ongoing travels. A key one is in being able to use feelings more assertively to guide my actions.

The wisdom of feelings

Feelings can seem overwhelming but I’ve discovered that, if I reframe feelings from being things that block me, to things that inform me, I can move through life’s challenges that bit more easily, quickly and productively.

“if I reframe feelings from being things that block me, to things that inform me, I can move through life’s challenges that bit more easily, quickly and productively”

There are two broad ways I do this, so let me share them with you. One means focusing on practical things that your feelings might be quietly nagging you about. The other means digging deeper into feelings to discover whether there are beliefs you’re holding about yourself that are past their sell-by date. Here are some self-coaching questions that you can use for both:

Practical things

  • What might this feeling be challenging you to give more thought to? For example, if you’re suffering doubt, fear or anxiety, and what you’re telling yourself is, “I’ll never make enough money,” do you know what ‘enough’ looks like? And…
  • What can you do to address this feeling directly? Sticking with the same example, you could develop your personal budget, understand what your bottom-line budget is, do some informal research to test what people are charging for the kind of work you want to do, and test whether, assuming you can market yourself successfully, you can charge enough to cover your bottom-line.

Digging deeper

  • What’s this feeling really about? Yes, there will be a large part of it which is really about the change you’re making. But what else is it about? In the “I’ll never make enough money” example, where did you first learn that money was a scarce resource?
  • What are you believing about yourself in order to experience this feeling? What are the words that go along with the feeling? “I’ll never be good enough,” might be an example. “Other people would make a fortune, but not me.”
  • Where, when and from whom did you learn these things? Chances are a parent either overtly or otherwise inferred that you weren’t good enough and that you had to go along with other people’s ideas of what good was in order for you to feel okay about yourself.
  • What would you rather choose to believe about yourself now? For example, “I can be successful on my terms”; “I can make money and be okay.” Say your new belief from that solid, grown-up part of you that knows it’s already true.
  • How does rewriting your belief make you feel? The chances are that, thinking differently about yourself will chase away less resourceful feelings, and free you up to get on with the next bit of your freelancing journey.

So, rather than have your feelings hinder you, allow them to tell you of the practical things you need to be considering and the emotional things that need some work. And see where all of that takes you!

This has been the second article in a series of three articles on quitting corporate life. Feel free to subscribe if you don’t want to miss the third installment, which is on the subject of risk-averse freelancing.

Related posts:

  1. Risk-averse freelancing
  2. How to quit corporate life

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