09/25/2012 11:44 am ET Updated Nov 25, 2012

Stay Happy at Work, or Move On - How to Know When the Time is Right

Here's a question I get asked a lot: "How do I know when it's time to get a new job." Yeah, we try hard to keep a job alive and vibrant, colorful and inspiring. But for most of us, there inevitably comes a point where it's time to move on.

A workshop participant once expressed his concern to me about these moments of transition. He couldn't understand how a person (me) could move from one job to the next or from one industry to the next without, in his words, "giving up all of the knowledge and advantage that you've gained." I'm not sure why he thought you had to give things up in order to move forward in your life, but it got me thinking.

I've moved from professional theater, to the film industry, to the Dotcom world, to the field of social entrepreneurship, and into technology product development. Last year, I wrote a career development book, and now I work as a consultant, strategist and "business doctor". Yet, I don't feel like I have ever given anything up. In fact, it feels like quite the opposite -- it feels like I've taken everything along with me. But how do you know when the time is right?

My old agent in Hollywood once told me that you should "Stay at a job until it makes you physically ill. That's when you know it's time to move on." I think waiting until you're "physically ill" is way too extreme. But there are other kinds of signs that you can look out for.

1. Are you engaged?
Every few months, ask yourself, Am I engaged with my work? Do I like what I do? What kind of contribution am I making? Am I fulfilled? Analyzing what you do for work on a regular basis is an ongoing reminder that work is a place to grow, not a place to stagnate. Remind yourself why you accepted your current position. What were you looking to achieve? Do the things that you identified still make sense? If you find yourself bored, stressed, or disinterested at work is it because you've been delinquent in nurturing your career? Have you stopped caring about your work and now it is repetitive and uninspiring? If you AREN'T engaged, it's time for you to re-up your commitment to your job. Look for new responsibilities that you can take on. Offer to manage something that no one else raises their hand for. Ask your boss if you can shadow her at meetings. Before you know it's time to leave, you need to know that you have explored all the reasons to stay. If you've done that and you're still not happy - it's time to move on.

2. Do You Feel Like Your Work Matters?
As a person, you are growing and changing all the time. You're gaining new skills, new insights, and developing, modifying, growing, and transforming yourself. So is your Company. And as your Company changes, it's important that your work still matters. Who wants to have a role where you're no longer making a difference? It's important to be in a constant cycle of evaluation at work. If your work and your role shift, you may find that you're not inspired in the way you used to be. It's important for you to understand where your unhappiness is coming from, because your discontentment might be caused by things that you can or can't control. If you have control--figure out how to fit in. If you can't - it may be time to move on. Life's too short to be unhappy at work.

3. Have you grown?
Here's something I've noticed: over time, our Passions focus, our Interests expand and our Skills grow . Does your work fulfill your Passions? (see video about finding work you are passionate about). Are you still engaged and interested at work or have your Interests changed? Are you continually learning new Skills or have your mastered all that you can?

Most people desire to do work at the place where their Passions, Interests and Skills intersect (see video on Finding The Sweet Spot). I think this is an imperative if you want to remain happy at work. Keeping this work "fire" alive means that, from time to time, you need to find something new to do. This isn't a bad thing. Steve Jobs, founder of Apple, once said during his now famous 2005 Stanford University commencement speech, "You can't connect the dots looking forward. You can only connect them looking backwards, so you have to trust that the dots will somehow connect in your future." If you've grown out of your job, it might be time to go find a new dot to stand on. It's at this point you KNOW it's time to move on.

So then what? There are a vast many roads you can take to evolve. You could try:
• A similar job at a new company in your same field.
• A higher ranking job at a new company in your same field.
• A completely different job in your same field.
• A similar job at a new company in a different field.
• A completely different job in a different field.
• Working for yourself.
• Going back to school.

The possibilities for creating opportunities in your life are endless. These moments of change are exactly the thing you need to bring color, vibrancy, and excitement to your work life. Leaving a job, or even getting let go from one, presents you with a huge, open world of possibilities if you choose to view it that way. Think of these moments as a gift--a time not of loss, but a time of infinite gain. Happy hunting!