Career Poker: Knowing When To Cash In Your Chips

Perform a quick Google search for advice on exiting or entering a job and you'll find millions of articles dedicated to helping you make the critical hold 'em or fold 'em decision. Most of this guidance, however,  provides a very reactive, even passive formula to decision making. If you simply wait until you're dissatisfied with your current role or presented with a better option, you're paying huge opportunity costs in the form of unnecessary angst, frustration and inefficiency. Proactive career management requires a tops-down look at these decisions.Admittedly, I'm a horrendous poker player (seriously, don't even ask me to shuffle cards) but the dynamics of absorbing environmental cues, adapting to uncontrollable circumstances and risk management are a great blueprint for building better career decisions.

1) Know how much you can lose

In poker, folding a hand isn't losing - it's quitting before you lose. Amazing winners are awesome quitters who limit their losses on bad hands. A winning game plan starts with a strategy for losing the right way.

How much are you willing to bet and what are the indicators that signal you're losing? Good poker players don't play more than 50% of the hands they are dealt. Each one has a starting hand requirement that determines when to hold 'em and when to fold 'em.

2) Play tight and aggressive

There are 169 possible starting hands in Texas Hold 'Em. Tight and aggressive players limit their play to only the top 10 hands - or about 6% of the hands dealt. Career poker requires each player to predetermine and measure exactly when to bow out.

I started my new role at Intuit 13 months ago and within the first 6 months I created 3 requirements that would signal its time for me to fold:

#1 - I'm in the way. My background and skills are insufficient to lead the team and there are better candidates present. Simply being temporarily insufficient isn't a deal breaker because that doesn't mean you're not the best fit for the role. It just means you need to learn and get to a break-even point faster.

#2 - My leadership and management approach are no longer a fit for the requirements to be successful. There's rarely a need to force a square peg in a round hole.

#3 - I fulfill the initial charter of my role (launch and lead a new Center of Excellence) and can expand my scope for greater impact in another capacity .

3) Count your chips

What's the market compensation range for someone in your field with similar skills and experience? Don't know? Find out using Glassdoor or any number of websites that provide a peek inside the salary mechanics of major companies.

Winning is not solely based on income but maximizing your earning potential is a significant contributor to future opportunities. If you're underpaid by 30% or more it may be time to address the value discrepancy or look to roles that provide more equitable compensation models.

4) Higher stakes mean higher risks

What's the biggest difference between a poker game with $2 stakes versus $20 stakes?  

Skill. As the stakes rise so does the average skill level of the other players. Mastery of a low-stakes game does not translate into continued success at higher levels. Smart poker players are intentional about where they play and who they play against.

More often than not, your pursuit of higher positions and income is also a pursuit of more responsibility. Do you want your boss's job? Do you want your boss's boss's job? Think about it before raising the stakes on your own game.

5) Pay attention to the other players

Poker is a game of odds and observation, with opportunities to flex both sides of your brain.  While you're watching the cards don't forget to keenly pay attention to the other players for tells, bluffs and play styles that influence your success.

One supremely beneficial tool in the game of career poker is LinkedIn. It's a great tool for identifying individuals who have positions you aspire to and then mapping their journey.

  • Do they have MBAs?

  • What's the average age or tenure in a certain industry?

  • What skills or past experiences are a common thread among certain roles?

Another great observational tool on the job is the lost art of asking. Many senior leaders are refreshingly candid about their career history and offer simple advice for moves you should emulate or landmines to evade.

Have you ever seen someone move into a high-profile role or promoted to a position ahead of their time? These aren't accidents. They are the result of patiently and intentionally building up career value (chips) over a period of time and leveraging this value to place well-timed bets when the cards are right.

Like anything worthwhile, it's much easier said than done but the rewards can far outweigh the risks if you're willing to invest the time to truly build a career, not just a job.

I would love to hear your thoughts. What are your requirements for doubling down on a role or taking a bet in a new position?

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