When Is the Right Time to Take a Career Risk?

by Salary.com Staff - Original publish date: December 4, 2013

Your Values and What You Value Are Always Changing

Christmastime is rife with financial responsibilities, so along with that new gym bag and must-have designer shoes, you’re probably thinking about looking for a new job, too. And a big, shiny paycheck to go with it!

The biggest compensation boosts come when you leave an employer for greener pastures (there’s a reason they call 'em that). How much of a bump depends on your ability to negotiate, market demand for your skills, and flexibility. In other words, are you willing to relocate to make the really big dollars? (Why, yes…yes, I am.)

Decade to decade your value as an employee changes, typically in the upward trajectory, but so do your personal values. The risks you take in your 20’s and 30’s are akin to career suicide in your 40’s and 50’s. Some moves are inevitable, foolish, forced or highly rewarding. Before you fall for the flash of an ambiguous title in a lofty institution, or trade your security for an ambitious start-up, do the hard work of due diligence AND soul searching.

Work should feel a bit like play, right? Be aware, the devil that you don’t know can actually BE a devil. Something that sounds too good to be true usually is, and all that green can quickly take on a nasty shade of gray.


If you’re going to take a career risk, do it now. Screw the student loans. There will always be some huge financial responsibility you can use later on as an excuse to hold yourself back like a mortgage or YOUR kids college tuition.

Right now you have time on your side, and a lot of energy. Don’t get sidetracked by the light-weight benefit plan of a startup, or a boss who happens to be the same age as you. Go for it! This is a great opportunity to put your fingerprint on the company culture and witness an entrepreneurial endeavor first hand.

If it doesn’t pan out, you’ll be that much richer in experience. From your vantage point (“I’ve already done a startup”) you will smell the duck coming long before you see it waddling and quacking. Plus, you’ll have an awesome story for the next group of co-workers at the “BYOB” water cooler.


Have you started contributing to your 401K plan yet? No? Well, ok, but that’s your priority when the enrollment period comes around again.

Career risks at this point are more calculated, spurred by 8 or so years of honing and refining your skills, not to mention the highly desirable paycheck that comes with making a critical move into the next level or a competing company. Also, your network has matured a lot from the alumni associations and colleagues you met throughout your 20’s. This is the ideal time to cull your professional contact database and strategically let people know you’re keeping an eye on the job market.

If you’re planning a family, however, you may want to consider what you’ll be giving up if you leave right now. As a new Mom or Dad, having to prove yourself all over again to a demanding boss while dealing with the day-to-day stress of managing a family may be a hassle you don’t want right now. Working for someone who “gets it” is a situation worth hanging onto until you have your feet underneath you and a solid support system in place.


Things really do get better with age. This is a time of richly creative, bountiful opportunities that seem to fall out of the sky. It took two decades of building your experience, but now there’s a seat for you at the big kids table.

The competitive hair-pulling (your own or someone else’s) of your early professional days are hopefully well behind you, and almost everyone in your sphere is contributing to your growth, and you to theirs. Sounds kind of idealistic, doesn’t it? Well, it truly is both a peak and a plateau worth hanging out on for a while. Maybe a little less excited about making changes, and not always readily agreeing with younger executives around us, but that’s the arrogance of experience and you’ve earned it! Still flexible enough to listen before making up your mind, and not afraid to say what you know is true in an authentic and genuine way. By mid-40’s, boldness is tempered with patience and the ability to let things play out as they are meant to -- not rushing in, but not resting on laurels either.

You’ve seen enough to know a unique opportunity, and when someone is trying to shine you on. Deliberately invest in those companies and individuals whose values align with yours, and be less willing to compromise on your integrity. Sleeping soundly has become more important than ever…for body and soul.


Time to switch it up and try something different. If you are restless and ready for a new challenge, but not sure where to start, try mentoring a young company. You have nothing to lose (a few hours a week?) and everything to gain by sharing your knowledge, experience and a little of your energy to help make the journey a bit easier for someone else.

In the process of doing so, you will not only experience a shot of renewed confidence, you may get recommended for a part-time consulting gig or a full-time role. Reinventing yourself is never an easy process, and finding the time to give back often means a trade-off on personal time. But the bottom line is, in order to stay relevant you have to keep exposing yourself to new situations, people and technologies.

The ideals of your teens and twenties often come back to find you during this decade of work-life. You now have the experience, as well as the passion and energy, to pursue those dreams. By now everyone else has figured out that you were onto something! The time is now to start planning out a more aggressive professional growth strategy if you were unable to keep contributing to your 401K/retirement funds over the past seven years. If you aren’t already doing so, you should be maxing out your 401K contributions and seeking a more generous vacation package, and severance agreements, if available.

60-somethings and Older

You’ve never been in a better position to contribute to the world. Look at everything you have learned over four to five decades of hard work! Have you started writing that book yet? Maybe that’s a little ambitious, but the collecting and recording of your accomplishments can provide so much intrinsic reward, you’ll be surprised at how much you’ve done!

By cataloguing your experience; new discoveries, big wins, obstacles overcome, and the list of people/organizations you have helped, you can recapture those moments and add them to your LinkedIn profile. Key word searches for specific skills, or exposure to certain companies and industries, can increase your search ranking and launch conversations with people who really need your help now. Your resume is a living document. Keep it updated and available for review at all times.

The value of a well-documented career should never be underestimated. Give your time wisely, but don’t give it away. Your value as a material expert should be compensated fairly. If you are working with a small company holding very short purse strings, negotiate for free office space, use of their equipment, free parking, payment of an annual professional association dues, or even a gym membership! If it’s a startup and you’re being asked to contribute regularly, go get yourself some equity. It won’t cost you anything, but could pay off down the road -- hopefully, just in time for retirement!!

Use Salary.com to Help You Get Paid Fairly

Regardless of what stage you're at now, you'll need to negotiate to be paid fairly. Luckily, Salary.com can help.

The first thing you should do is research, so you're able to come to the table armed with the knowledge of what your job is worth. Use our free Salary Wizard below to find out what's a fair salary for your position. You can enter your location, education level, years of experience and more to find out an appropriate salary range before you negotiate.

Good luck.