One year ago today, I walked into my boss’ office at the company I had worked at for over a decade, and I quit.

It was not a hasty decision, nor an easy one. I was leaving a senior leadership position at a multinational firm to start my own career coaching and leadership development company from the ground up, in a country on the other side of the world from my native Australia. As the news spread, I got a mixture of reactions that ran the full spectrum from, “You’re crazy!” to, “You’re such an inspiration!” (thankfully for my resolve, they were skewed towards the latter…)

The truth was, I felt backed into a corner. I was experiencing conflicts between my personal values and those of my workplace that I had never experienced before, and it was making me physically ill. When a doctor tried to prescribe me two separate antidepressants and a sleeping pill for what she diagnosed as situational anxiety, I decided to try and solve the cause of the problem rather than treat the symptoms. So, I turned all of my attention to creating the business I had been dreaming about on and off for my whole career, and combined my leadership experience with my coaching education to create Light Yourself Up.

The first year of being my own boss has been an incredible roller coaster of emotions, and I would not change it for the world. Despite being slightly surprised that I’m not a multi-millionaire just yet (as all of the podcasts I listened to in the lead up to my leap suggested I would be), I am delighted with the way my business is evolving.

The situational anxiety did indeed disappear when I removed myself from the offending situation. No longer dealing with sleepless nights and chronically elevated cortisol levels, my physical and mental states have improved dramatically.

Even so, there are things I miss about my old corporate gig. Things that I never read about during all my research before I made the leap, and most of which came as somewhat of a surprise. So I thought I would take the time to reflect upon and share the things I miss most about having a job, to help others who are contemplating a similar move.

1. Structure
The best and worst thing about working for yourself, in my opinion? The lack of structure. After spending my entire career in a highly structured corporate environment, the freedom to set my own schedule seemed like the ultimate productivity hack. After all, I know when I do my best work, and having the liberty to throw myself into it at those times, and take care of myself during my body’s natural “downtimes” would surely make me more effective. Right?

In my first year of being an entrepreneur, I quickly learned that motivation seems to occur naturally for me at two levels – zero and eleven. Meaning that I was either working all hours of the day and night in a flurry of inspiration, or searching for the secret recipe to get moving again.

One of the most valuable skills I have learned this year is to understand how my body signals that my mind is over- or under-stimulated, and to be disciplined in moving back into balance when that happens. For example, when I am feeling stuck, I know that my best course of action is to stop and reflect on what’s going well and what’s not going so well. From that I put together a plan to double down on the things that are going well, including the first baby steps I need to take to achieve that.

2. Knowing the Rules
Related to but distinct from structure, there is a lot to be said for knowing the rules of the game. After working for the same company for over a decade, I knew exactly what I needed to do to succeed in that environment. Note that this knowledge can also mean that you know what you need to do to avoid getting fired!

The challenge came when I was no longer prepared to do what it took to be successful in that environment. While this was a personal decision based on a variety of factors, it created stress in other areas by creating a goal conflict with my desire to have a successful career.

Leaving that environment to start my own business landed me in a completely new game, whose rules of engagement I knew little to nothing about. I was completely oblivious to patterns of cause and effect, which could make efforts to grow my business intensely frustrating! I handled this using a simple re-framing technique suggested by the coach I was working with at the time. I decided to view my first few months as if I were in a laboratory, and everything I did was an experiment. This appealed to my scientific nature and made the “newness” all around me more intriguing than terrifying.

3. Lovely, Lovely Money!
In case you haven’t really thought about it, let me tell you that leaving a comfortable corporate paycheck to chase the dream of starting your own business can be terrifying from a financial perspective.

Aside from a possible drop in income when you start out (which most entrepreneurs are savvy enough to have planned for), moving to a relatively inconsistent income is a massive adjustment to make.

If you are considering making a change like this, practical financial planning is a must. Of equal importance though, are understanding both the role money plays in your perception of yourself, and you and your partner’s shared goals (if applicable). Many people skip these crucial elements and find themselves challenged by unexpected identity crises or relationship problems after they’ve made the change. An assessment of your personal values and an exploration of your shared definition of wealth with your partner prior to making the change will go a long way to helping with this.

4. People
For me, the hardest things to leave behind when I quit were the people I truly cared about. There were people I worked with who I genuinely enjoyed seeing each day, and who I miss now that I’m no longer in that office environment.

Paradoxically, this also ended up being the easiest to deal with. Although I may not see them every day, those people have remained in my life in various ways, and now when we see each other we tend to talk more about things unrelated to work!

The other side of this is that creating my own business has allowed me to become very intentional about the people I choose to work with. Rather than being thrust together because of a common employer and hoping for the best, I now have the privilege of seeking out my “peeps” and building amazing things with them!

5. Scaled Impact
This one came up rather unexpectedly for me, and is a great example of the fact that no matter how much planning we do for a major change, there will almost definitely be something that we don’t account for. In my preparation, I had carefully considered my values, what I loved most about my previous career, and had tried my hardest to incorporate these into my new venture. One thing I missed was the satisfaction that comes from having a large organization with lots of talented people at your fingertips. It turns out that major project execution is significantly simpler when you have a team of twenty working on it!

This piece of learning has given me something to work on as I grow my business in 2016 – how to build great teams to help me help even more people build a career and leadership style that they love!


Of course, the things I love about running my own business far outweigh these things that I miss. Doing work that I know is having a direct, positive impact on people’s lives is nourishing for my soul. Having complete creative control over my business is ultimately satisfying. Having a schedule that is generally flexible enough to accommodate my passion for playing the trombone has allowed me to make all kinds of breakthroughs in that regard in the last year. And not commuting for 1.5+ hours every day is pretty amazing too.

My advice to those considering making a similar change? Before you leap, get to know yourself really, really well. There will still be surprises, but the more you can anticipate, the smoother the ride will be. I hope that my own journey can help you along yours.

Have you ever made a massive career change? What was your biggest lesson from the experience?

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