How Much Potential Reward Merits Career Risks?

A friend posed a question recently: In our career, are we bold enough to soar like an eagle, or are we chicken – bound to the safe ground and presumed limits.

Sometimes, it’s easier said than done; the stage of career is a significant factor in making decisions about potential risks, which can come in a variety of forms. A fresh-out-of-college new-in-the-workforce employee has a much different vantage point than the tenured professional with money in the bank and desire to start their own company. That said, we’ve likely all weighed and considered making substantial career risks against the potential downside at varying levels of our career.

Do we sacrifice or gamble a steady yet unfulfilling role because it pays the bills for our family? Do we leave Corporate America and structure and benefits for the unknown because it scratches an entrepreneurial itch?

Career risks can absolutely pay off with financial and personal gratification and reward. They can also go horribly wrong – no matter how much thought goes into them. There are most certainly rules and principles you should apply when making these life-changing decisions.

  1. Never gamble what you cannot afford to lose, but don’t be afraid to gamble something you can live without. If you are in a role that can be easily replaced and the proposed transition will immediately improve your finances or your ability to move up, it’s worth considering. Be careful, however, to take too many “steps back” – I hear all the time people saying, “Yeah, I’ve got to take a step back, but in a few years I can move up.” Frankly, that’s true most anywhere and no matter what you’re doing, you’re going to have to pay dues to go to the next level. If you leave, any dues you have already paid are likely forfeited permanently. Certainly, they may help gain you greater footing when you start out in a new role or new company, yet you’re starting all over at this new company at the bottom of the totem pole. You’re once again the newbie. Your tenure is gone.
  2. Is the grass really greener?  Do your research. The nice thing in this day and age is that social media like LinkedIn allows us access to just about anyone. This empowers you to talk to people who are in the know about the specific opportunity – people who have done the job, do the job, know about the job. Look, I get it: when you aren’t pleased with your lot in life, it’s so easy to look at something else and be allured by what looks great from the outside. I’ve seen people job hop repeatedly, always hating just as many aspects of the new job or company all the while having to start over again and again and again. Investigate the other opportunity. There will be some that are better, some worse and some a wash; you can only find out as much as possible to help you make an informed decision. If you aren’t sold you’re making an upgrade, you should probably shy away.
  3. Are you at a stage in life and career where you can make a risky move? If you’re paycheck to paycheck, supporting a family (meaning others are part of the decision-making process and kids are depending on you), just made a major purchase, or are in the midst of or eyeing major change, making another one in the form of career may not be wise. Do the math based on the worst possible scenario: if this risky move results in you completely falling on your face, how long could you sustain your current responsibilities while in search of something else? This can absolutely aid you in the decision. Sometimes we have to look at a potential opportunity, realize it simply is not feasible – accept that fact, and move on.
  4. Is the change reversible? In a favorite superhero film, Superman foregoes his powers so he can live as a human with Lois Lane. Scenes later, the world is terrorized by a serious threat and he’s got to beg and plead to his deceased, holographic Kryptonian parents to get his powers back. If there is a chance of going back to the gig you’re leaving in the event things don’t pan out, this certainly minimizes the risk and can make the decision a lot easier to make. If you are in essence burning a bridge or sealing off what you do now, very carefully weigh those consequences.
  5. How often do you make career risks? If you’re bouncing from job to job, what impact is that having on your career and your prospects? That can show an employer you won’t be around for the long haul and could inhibit you. Are you improving yourself each time? Do you have more hits than misses? These are all things to consider, because if you make a lot of risks and they typically don’t pan out, I’m not sure what would lead you to believe your next risk might. But if you have been really stable and devoted and hard-working and things have not panned out toward your long-term goals over a decade or two of dedication, perhaps a change of scenery brought about by a little leap of faith is not such a bad idea. It’s all about perspective.

Obviously, when making these types of important decisions, it is important not to rush into them. Don’t react to a setback at work by resigning or applying to 20 internal jobs. Don’t get all worked up and start telling everyone about a potential path you’re exploring. Absolutely look into and explore potential paths to better yourself. If and when there is a decision to make, try to know everything you can to make the most informed decision. Then commit.

The more knowledge and experience and stability, the better your decision-making process evaluating career risk will be.

Sometimes all signs can point to taking the chance and the chance still does not pan out. The advantage of taking the risk is you don’t look back with regret; you can grow to accept your role and function, and perhaps even pursue other passions on the side if you aren’t being fulfilled in your career. Many of us accept roles that are not our true passion, and we do so for money, for stability, benefits, and security for ourselves and those we love. Nothing at all is wrong with that.

We may regret taking a risk, but if we do our due diligence and walk through the proper motions to get there, chances are likely we will be able to live with our decisions now and in the future.


Carson V. Heady has written a book entitled “Birth of a Salesman” and sequels “The Salesman Against the World” and “A Salesman Forever” which take the unique approach of serving as sales/leadership books inside of novels showing proven sales principles designed to birth you into the top producer you were born to be. If you would like to strengthen your sales skills, go to

Heady posts for “Consult Carson” serving as the “Dear Abby” of sales and sales leadership. You may post any question that puzzles you regarding sales and sales leadership careers: interviewing, the sales process, advancing and achieving.

Question submissions can be made via LinkedIn to Carson V. Heady, this Facebook page: , Twitter via @cvheady007 or e-mail at or you may post an anonymous comment as a reply to my WordPress blog at the bottom of this page:

About cvheady007

I am a Christian, Husband, Dad, workaholic and author. Biography Carson Vincent Heady was born in Cape Girardeau, MO, graduated from Southeast Missouri State University and moved to St. Louis in 2001. He has served in sales and leadership across Microsoft, AT&T, Verizon and T-Mobile. Carson is best-selling author of the Birth of a Salesman series, the first book of which was published by World Audience Inc. in 2010. He released The Salesman Against the World in 2014, A Salesman Forever in 2016 and Salesman on Fire in 2020. He is also featured in Scott Ingram’s B2B Sales Mentors: 20 Stories from 20 Top 1% Sales Professionals. Carson is a 7-time CEO/President’s Club winner across 5 roles at AT&T and Microsoft and National Verizon Rockstar winner. He has been recognized as a top social seller at Microsoft and is consistently ranked in the top 25 sales gurus in the world on Rise Global. He is included among the Top 50 sales authors on LinkedIn. With over 330K social followers, Carson has also been interviewed on over 30 sales and leadership podcasts, by such luminaries as Jeffrey & Jennifer Gitomer, Jeb Blount, Brandon Bornancin, Sam Dunning, Larry Levine, Darrell Amy, Scott Ingram, Thierry van Herwijnen, Jim Brown, Sam Jacobs, Luigi Prestinenzi, Donald Kelly, Marylou Tyler, George Leith, Pat Helmer, Eric Nelson, Ron Tunick, Jeff Arthur, Mary Ann Samedi, Jean Oursler, Andre Harrell, Marlene Chism, Bill Crespo, Matt Tanguay, Josh Wheeler and Chad Bostick. He has also co-hosted the Smart Biz Show on EG Marketing Radio. His articles have appeared in several noteworthy publications such as SalesGravy, Smash! Sales, Salesopedia and the Baylor Sports Department S3 Report. Carson lives in St. Louis, MO, with his wife Amy and daughters Madison, Sidonia and Charlotte.
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