When to leave your job

I worked for many companies (Starcom, CBC, PHD Media, National Post, Leo Burnett, Coca Cola) during my career and i have learned a few lessons about changing jobs and when the best time to leave is. Knowing when to leave is a skill. Practically speaking you need to balance your personal reality, money, and life...but here are some other things to consider as you make your decision.
1. Do you love (or like) what you do. What really matters.
I believe you need to. I used to spend over 75 hours a week at the office. I needed to like it and even love my job. And I did love it, until I didn't. Then I started the process of contemplating my next move.
For me the reason I left because was that what mattered most to me changed and that was a combination of leadership, vision, and responsibilities.
Here are some important questions to ask yourself when thinking about leaving a your job: a) what's important to you; b) what impact do you want to have or want to have; c) what are you contributing to; do you understand the "why" of your organization. d) do you believe in the mission of the company you are with.
It's really important that you're in a job that is helping you to have an impact. If you're not motivated by what you're helping to build, or what you're contributing to it, you should be working somewhere else. The other important question is does the job align to your values. I find this is a huge one as you get older.
If you don't love it, don't feel you are making a positive contribution, understand the role you play in the scheme of things and believe in their culture and values then it is time to leave.
2. Are you building skills or learning
What are you good at and what do you need to learn. If a job helps provide you with learning it may be worth staying. At my last year, I learned to transition to becoming an executive leader; I become a better public speaker; I learned about great advertising and a little about technology. In my new job, I took it primarily because it would help me better understand the nascent world of tech...and that is a huge motivator. You want to work somewhere that will give you leverage on things you need to learn and experiences and skills you need to develop your career.
3. Your boss...do you need a visionary or an executor
People leave managers not companies. In my career I had a handful of great bosses who were coaches, mentors, friends, supporters. I cannot tell you the impact they had on my career. Before you take a job look for those visionaries. Take less money to work with them. They are career makers. But when that dynamic changes you need to think hard about staying. Some say the only way to fix a bad manager is to find new one.
That is not to say that great executors cannot make a great boss. They can but I believe you will learn more with visionary leadership.
Important to understand the difference between these two types of leadership styles and jump into a new role with eyes wide open.
4. It is better to run to something that run from something
Regardless of your situation in your current role, don't take any job to leave. I have seen countless people make multiple mistakes when jumping to quickly into something that doesn't really offer what they really want. Plan out a 6 month window. List out companies and people you want to work for and with. Start networking, researching and meeting them. Inquire about process; offer to meet for a coffee to gain information; find recruiters that you trust; find great mentor to help.
There are no unicorns in the world of work and no situation is perfect all the time. But there are a few things you can control. If you can pick your job then find the best person to work for and find meaning in the work. If after reading this you are still stuck and need an ear to talk to , contact me and I will do what I can to help.
I have seen many people take jobs that are misaligned. They thought they took one job and ended up with another. While no job is perfect and all require flex and pivots there is a huge difference in skill set and culture if you hire a strategy leader but really need an enterprise manager.