How do you know when you're ready to move on?

I’ve been chatting with a friend lately who works at a great company that has alot of potential and overall enjoys the work. Her biggest issue is that shes not learning anything new and because the design function in her larger corporation is small, there is not much room for her to grow not only in status but in compensation aside from climbing the general pay scale ladder. To me this seemed simple, and I said she should leave. Her problem though is the thought of her current company’s success is clouding her thought to leave, and this got me thinking, when is the right time to leave your job in search of something new? I think about people that might work for theoretically great companies (there are some companies who appear great, but its kind of like the "dont meet your hero scenario) like Google, or perhaps something like IDEO, know when to leave? I’m sure this is a tough question from any perspectives but it got me thinking and I wanted to hear the groups thought.

For me leaving Nike and frog I considered a number of factors when deciding to leave:

  1. had I learned pretty much everything I could learn?
    After shipping 400+ shoes at Nike, and being a part of winning pitches for Google, Intel, and Honda at frog I felt like I had learned a lot.

  2. had I done everything I wanted to do?
    At Nike I worked in NSW, Jordan, and Converse, at frog I had completed several kinds projects that the company had never done in its history… I could ave done more at both, but I felt good about my contribution,

  3. was the opportunity I was leaving for worth it (you only put once)?
    In the case of Nike, I was leaving for frog, in the case of frog, I was leaving for an unknown quantity, but I was at the point in my career where I wanted to make a mark. I didn’t make nike or frog what it was. This was an opportunity to create and I got to do a lot including designing the HQ and naming the company… that made it very hard to leave, but at the end of the day I felt like I had built the brand, team, processes, and shipped a lot of product, so it was time to move on to another challenge!

In the end, I think more people regret not moving on to try something new vs the opposite. Sure there are some days when I think maybe life would have been easier if I stayed at Nike, maybe I’d have most stock, maybe if I stayed at frog I’d have more prestige, but 99% of the time I’m happy I had these adventures and didn’t play it safe. The alternative is staying too long and then getting stuck (note, you are never really stuck, but it can feel that way).

If the company has good upward momentum, potential, making money and so forth, those are going to be more tangible up-sides than going to see if the design grass is greener someplace else. I don’t buy for a second that a “great company” also will have the problems: “shes not learning anything new and because the design function in her larger corporation is small”. If she has a good albeit small design role but the company has solid leadership and your friend is intelligent and enterprising it could be a great opportunity to expand the design function, learn more about the business, practice Capital D Design Thinking on a strategic level.

That, or five plus years at one company, then its probably time to look around. But again, the grass is never greener.

Sometimes the grass is even greener than it appeared, because distance blurrs and greys everything.
(hints to C.D. Friedrich landscapes)

But really. Give life a try! For heavens sake live !

Knowing when to leave is a personal decision and everyone prioritizes it differently. I have left for these reasons:

  1. First things first, I am a father and husband before I am a designer. Hostile work environments, or if a job does not allow me to be my whole self with my family I will leave immediately. Life outside of work is, in my opinion, more important than life at work.

  2. You have to have passion for the category you work on. If you are not passionate about the work you do then you will never put in your best work. No matter how great the pay, level, etc… is; move on if you do not care. You are wasting your time and your employers.

  3. Am I being challenged anymore? I spent my first 11 years of my career at one of the largest food/candy manufactures. I was designer number one and by the time I left we had built a global team. In this role I did everything from package design, to food design, to implementing/growing design strategy. I built practices, and really changed the way people viewed design. But after a good run, I started to notice I was taking on the same challenges. I felt I needed to move on to take on bigger and larger challenges. This was my first real career move and one of the hardest. I had developed some of the most meaningful business relationships that have become great friendships to this day.

  4. Kind of related to number 3, I have always kept a small Moleskin notebook with career goals, both short-term and long-term. This is a tip I got from YO BTW. I also pay attention to industry trends and how they relate to my career goals. I consistently ask myself… Am I moving in the right direction? Is what I am doing now going to help me grow professionally in the future? Am I gaining the skills to stay relevant?

While working for some of the largest food companies with award winning design organizations and my goal book in mind, I decided to leave food after 13+ years. I loved the CPG food industry. I was very good at it, but I got to a point where I knew it was not fitting what I had put down as my career goals. I had wanted to impact the lives of people in ways that food could never deliver. I had just had life experiences such as having a baby and was curious what it would be like to work on experiences such as the baby/mom relationship. I also had goals of getting back to my consumer product roots and growing innovation within a product company. I knew deep down, it was time to move on.

  1. This one may not be related to your question, but sometimes your career moves are not by choice. All of us will most likely be part of some sort of layoff at some point in our career. When this happens I encourage you to take a step back and look at the positive. It’s a perfect time to gather all your skills and ask yourself what’s next? When this happened to me I was 15 years into my careers. I had led innovation in many different industries except for digital and services. I was approached by an insurance company that was building a Human Centered Design practice. They had some really interesting challenges. Not only were they trying to figure out what design was, but Insurance was a pretty f’d up industry when it came to consumer experience. I jumped head first into the craziness and that is where I am now.

I hope this helps.


Success of the company I work at will be the ultimate decider for me and make me want to commit to them for potentially my entire working life. That kind of commitment is often what companies are looking for, at least over here. Job hoppers generally have a harder time landing jobs already because of the reason that it seems they cannot commit and stick to something. Then to me comes room for growth in terms of design qualities, personally and for the business. Then come the extra factors like compensation and team vibe. It is a very personal choice. A single factor in someone’s life is often enough to be the deciding one.