In mid-summer of 2021 I was approached by a former colleague and mentor of mine about an opportunity. The company he works for needed a team leader to join them after some restructuring. My friend thought that I would be a good fit for the role and set up some meetings to see how the fit would be. I wasn't looking for a new job but I thought I'd go through the interview process, talk with my potential future boss and team and see how it went. For the first time in a long while I needed to think about what I wanted from a career which ultimately made me think about what I want in life.

Aside from a period of about 8 months in 2012-2013 I had worked for the same company since 2006. I've enjoyed my time there and I've been able to contribute to the company in a number of different roles, working my way from an entry-level support role to become manager of a new function in the organization. I would often get satisfaction from being able to overcome challenges but I would say that the general feeling of working there has been one of contentment. So when I was approached about an opportunity at another company I started thinking about what I would need to get more out of a job. I decided that a new job would need to make me happier than I was at my current job.

Would a change of company make me happier?

I was not unhappy at my current company. I've been given plenty of opportunity, had a great set of peers, had a great manager who supports me, and best of all had a great team working under me that really ensured our function within the company was successful. The new job would need to have the same and more to make me want to move. I didn't get the sense that there was more opportunity for advancement, better people, or a better team than I already had. Admittedly it's not really a fair to compare rapport you have with people you've worked with for months or years against people you've only had limited time to speak with over video calls during an interview process, but I couldn't be sure I'd be happier by changing those around me.

Would more money make me happier?

During the interview we did have a discussion of compensation. The salary was more but it wasn't large enough to make me want to leave. Back in 2012 I left a job I really liked for a 25% and ended up miserable, only to return to the job I liked at my previous salary. I did not, and still do not, believe that more money alone, would make me happier.

Would more time make me happier?

This is what I pondered longer and harder than any other aspect of the potential new job. There are two aspects of time that I considered.

Being at a small company for as long as I have you become known for certain things, and unless change is managed properly when you take on a new role you tend to bring old responsibilities with you. So for me the notion that I could come to a company with a clean slate and be able to focus on being a leader was appealing. But if I really thought about it,% that's a lazy approach. I could also find ways to unburden myself in my current job which would provide learning opportunity for myself and benefit the company in the long run.

Vacation time was another potential benefit I considered. The other company was offering 'unlimited' vacation. I had maxed out the number of vacation days at my current job. The stance the new company took on 'unlimited' was that everyone was encouraged to take at least 3 weeks off each year and you can take time off beyond that as long as the things that need to be done are getting done. There is definitely some appeal to this idea but I believed I would feel guilty about taking more time off than I was entitled to and might not actually enjoy more than the requisite 3 weeks.


Why should I feel guilty about taking time off? I give most of my waking life to the company and the rest of my life has to be scheduled around the time I give to them. I think I could be happy if I could spend my time how I want, walking with my kids to school, having coffee or lunch dates with my wife or my friends, learning a new hobby or going to the gym when most people are at work.

I would love to make my time my own!

Of course I can't just quit my job. A family needs money to live. My familiy and I have become accustomed to our lifestyle and while we could make sacrifices to lessen our expenses each month it just isn't realistic to expect my wife to be the sole earner while I indulge in whatever I feel like doing day-to-day.

I would love to have a way to earn money and not give up control of my time!

But what business is going to let me control my time and pay me enough to keep me and my family living the life we have. Or forget the life we have, what about the life we want!? What if we want to go on a vacation together, or go somewhere warm for the winter while we immerse ourselves in another language and culture? I can't think of any businesses that would be willing to let me work whenever, wherever, and pay me enough to afford it all.

I would love to go wherever I want, whenever I want, all while making enough money to afford it!

Aha! That sounds like a very happy and very free life! No job is going to give me that.