Decide If It's Time For a New Job

pirates (1).png

In my last post I explained how you need a plan if you want to go after a new gig this year. What about those of you that are on the fence? Not sure the time is right? Read on:

So, you're thinking you might want to jump ship from your current gig in the new year. There are a few questions you should ask yourself before you do.

At the heart of any life-change situation there are a few basic questions that must always be asked: Who?, What?, Where?, When? and Why?

If you’re not completely satisfied at your current job and are contemplating a change, you should take the time to ask yourself these same questions, or you just might find yourself in the same boat a few months after you just jumped. The answers might surprise you, they might not. But armed with the answers, you might find that you’re able to make some changes in your current job to make you more satisfied, or you’ll be equipped with info for any interviews you line up.

Who? Who do you want to work with that you’re not getting a chance to in your current workplace? Are you a Jr. Creative who wants more direct mentorship from the Creative Director? Are you a pink-haired, punk whose desk is covered in Star Wars figures and all your coworkers are beige clad, sensible heel wearing, squares? Are you a cabin boy who needs to learn the ropes? Literally? Would you prefer coworkers who were more like you?

At your current job, there might be simple ways to work closer to people you want to - just ask for the opportunity. Ask to be put on a project with that team or ask for a mentorship with a particular manager. If there is no possible way to work with the people you want at your current position, make sure to ask yourself, specifically, why you want to work with them. Is it to learn, to feel more comfortable culturally? Great, know what type of people you want to work with and take that info with you to your next interview.


What? What do you want to be working on that you’re not? If you want to make TV commercials, but you’re at an all digital shop? It might be time to move. Are you basically happy at your job but you just want to work on a different client within your accounts? That might be more possible with a few conversations with your manager. If you want to make hamburgers but you work in a chocolate shop? Then yeah - get that resume together.

Sit back and ask yourself exactly what it is you want to be working on and why you want to be working on that specific thing. Got the answer? Let the hiring manager at your next interview know exactly what you would like to work on and that you’re jumping ship for the opportunity to do it.

Enter your info to get your free "5 Big Questions to Find A Career That Makes You Happy" worksheets instantly!

We won't send you spam. Unsubscribe at any time. Powered by ConvertKit

Where? Where do you want to work? Not just physical location but what about the size and culture, of your current workplace isn’t satisfying? If it’s a matter of you working in the New York office but would be happier in London - ask for a transfer. Do you want to work in a small company but you’re one of thousands? Do you want to work in a multinational corporation, but you share your boss’ home office with the one other employee? Knowing what size of company you feel you make the most impact in is important.

Size tends to also affect company culture. “Culture” isn’t ping-pong tables, beer kegs and jaunty sea shanty sing-alongs. It’s the way the company operates and treats it’s employees. It’s how they get things done. If you want a younger-skewed, informal, non-profit giving culture but you work as a bond trader in a blue blazer - it’s definitely time for a move. If you’re generally happy but would like more ‘All Hands’ meetings so employees felt better informed? That might be a welcome suggestion to your manager.  

When? Do you know for sure you’re ready to jump ship? You’re 100% certain that you want to leave big-city life and go to work on a dairy farm? More power to ya! When do you want to do that? ASAP? After you have saved up a hefty money cushion? Before the next business quarter? Once you have a solid date, you can work back towards a clear exit strategy including networking, interviewing and notice giving.

Why? Back to the basic question. Why are you unhappy at your current job?A little self examination upfront can save you many tears spilled in the mailroom. If it’s a matter of a majestically larger salary bump - go forth and jump. However, if you’re happy but need a little flexibility in hours due to childcare, talk to your manager. If something can’t be worked out in your current situation to meet your needs, then yes. Jump.


If you know that it’s time to leave, and it can be helped, don’t jump to just the next available thing. Once you’ve networked your way into an interview for another gig, use the answers to these questions strategically. Interview the company, just as much as they are interviewing you. Make sure to ask who you’ll be working with, what you’ll be working on and what the culture is like. For true career happiness, knowing what particular ship you want to be on the crew of is key. Also, pirates.