The Career Inbox

Is the grass is always greener?

Landing your first job is difficult, but determining when to move on to the second job can be gut-wrenching.

Updated August 28, 2019

I often field questions from designers who are working through professional dilemma’s that don’t fit nicely into a textbook. Many have volunteered to open our conversations up to the public. Identifying information was removed for specific individuals or companies.

Designer Hey Chris, how are you doing? Your prior career feedback has always been beneficial, and I believe that your guidance was a significant factor when I got employed.

I have been working as a full-time designer in an enterprise company for almost two years. I am now thinking of a change. I got an offer from a company which is very similar to my current employer. They are giving me around 40% more than what I am currently making, and it is a high growth startup. What factors do you think I should consider before making the switch?

Any insight that you can provide would be super valuable.

Stock photo of hands at table Stock photo. source:

Chris There are a few key things to take into consideration before making any big career leap.

First, how happy are you in your current role. Specifically, do you have the right work/life balance? Any change is bound to cost you some control over your life in the short term. You need to go into this eyes open. You'll have more money, but you'll also have a new set of problems to sort out.

Next, what will this move allow you to do that you can’t do now? Sometimes this answer is very straightforward, like paying down debt. Other times, it is about career advancement. Everyone has different reasons, but you need to know what yours are.

Also, do you like what the new company does? No matter how much money someone throws at you, I don’t want you hating yourself every day that you get out of bed. It’s a big reason why I’ve walked away from jobs in the past. You can love the work, but if the people are toxic — it won’t matter. The inverse is also true. You can like the people, but if the work is dreadful, it’ll be a short-term move.

Finally, is it the right time in your life to leap. Every move has a little pain, but if your life is already hectic, that small discomfort could be agonizing. If nothing else, settle down life outside of work just to be prepared for possible turbulence.

Everything I have stated is me approaching this move ultra-cautiously. I focused this advice on helping you avoid surprises. Please note that everything could go completely in the toilet at your current job as well. The business could fail, an acquisition could occur, an asteroid could hit the office building — literally, anything could happen. It is far better to wander into uncertainty when you’ve fully considered the possible outcomes — which should include the possibility of this being a fantastic move.


Designer I did speak with the hiring manager and asked him all the questions above. I am overall feeling very confident about the new company. The only con that I could figure out is that my commute is going to get affected. However, I also understand that there is no gain without pain. :)

Thank you so much! Your advice has helped me significantly. It helped me two years ago, and it has made the difference yet again.

Have a question?

Your career growth is important. If you have a career question you’d like to have answered, email

Receive daily feedback and weekly meetings with Chris Courtney by signing up for monthly mentorship today!

Sign up today!