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A Sales Rep Looks at Sixty. What Really Matters in Your Career? Five Priorities.

I confess to being a Jimmy Buffett fan. It does not matter the weather or the location. A sunny beach day or a dark and cold Upstate NY winter day, his words and music have always managed to lift my spirits. One of my favorite Buffett songs was the inspiration for this article. In A Pirate Looks at Forty, Jimmy sings about a legendary Key West character looking back on his life and career with a mixture of sadness, a little warmth, and a fair share of regret.

Mother, mother ocean

I have heard you call

Wanted to sail upon your waters

since I was three feet tall

Mother, mother ocean

after all the years I've found

My occupational hazard being my occupation's just not around

Typically, I write articles about the mechanics of the job search process. Strategies and techniques to accelerate and win your job search and land an offer. Occasionally, I write about the broader and more overarching topic of work and career. Today is one of those days. When I listen to Jimmy Buffett sing about his 40-year-old pirate, I know that there are also a few career lessons we can take away from his words.

As the title of this article suggests, I am sixty years old and spent most of my career in the sales profession. Retired from the corporate world now, I have the benefit of perspective. The question I want to examine is what really matters in your career. When you are at the beginning of your career path or deep in the fight, you have one set of priorities. At the end of a career, you can look back and see if those were the right priorities and what do you get to keep when you merge off the fast highway and onto a slow country lane.

For simplicity and in the name of brevity, I will focus on just five priorities with which we all can identify. Money, Title, Recognition, Knowledge, and Relationships.


Is your career one long “show me the money” scene from the film Jerry Maguire? Yes, income is essential. We need to be able to pay our bills. And once you have money, it is natural to want more and more. At our family cottage, we have a spot on the wall where we marked our children’s growth from year to year. Income is a lot like that measuring post for your career. How much money you make in each position becomes a yardstick for how you progress over your career path. Make more money every year, watch your W2 increase from the past year, and your career must be moving in the right direction.

We also use salary and wages as a measure of our worth. Pay me what I am worth. We are conditioned to view salary or income as a reflection of our value to the organization. Does a higher salary or job offer equate to greater importance? That person makes more money than I do, so his (or her) words must matter more than mine. More money means greater job satisfaction, or so says this study from CNBC and Survey Monkey.

The Pirate’s Perspective: In your career, I think it is a lot more complex than simply stating that money equals happiness. At the end of my corporate race, I now have more of a Maslow's Hierarchy of Needs view on money. Once you have enough to meet your personal needs, the curve begins to flatten. Money can take you from a level of dissatisfaction to neutral in your career, but it can never make you love your job or your work. For that, you need something else (Hint: See Knowledge and Relationships).


Job titles are central to your job search and also another guidepost along the arc of your career path. I am deep into Season 3 of The Crown right now and have learned that a monarchy is nothing without titles. And in the corporate world, we place enormous importance on titles. Whose voice carries more weight in a meeting? The Financial Analyst or the Senior Financial Analyst? The Marketing Associate or the Marketing Director? Similar to salary and income, job titles confer a measure of self-worth and value to the organization. Job titles are just a more outward-facing public expression of that worth and value.

We spend the better part of our career “climbing the corporate ladder,” wanting to add to that title. Add Senior to the front of the position title or Director to the end of the email signature. Lead the meetings. Make the hiring decisions. Get the corner office. Throughout your career, there is no escaping the importance of titles. This article from the BBC shares research showing that job titles have the power to improve our state of wellbeing and sense of control. As long as we have hierarchical organizations, job titles will continue to confer a sense of responsibility, tenure, and advancement.

The Pirate’s Perspective: Over my career, job titles were important. I collected titles like merit badges. As soon as I had one title, I wanted the next best title. I told myself that I could not retire until I could add Vice President to my business card. But, as I sit here now, I cannot remember most of the job titles I held. And suppose I were to do a regression analysis and plot a line of best fit. In that case, I doubt that there was much correlation between my job title and the relative value I contributed to each team or organization.


Who would not want to receive an award, a compliment, or recognition for a job well done? Working in sales for almost 30 years, I was fortunate enough to win several awards. Crystal, plaques, trips, cash bonuses, merchandise, and even stock grants. Acknowledgment from management and peers that your contributions have value and rise above the crowd. Recognition can be a powerful motivational force in your career. Once you taste it, you want more recognition. Receiving the award feels good. Losing or missing out on that recognition can be painful. Just ask me about the time I missed out on the annual company President’s Club trip but received a holiday turkey as the consolation prize!

The Pirate’s Perspective: Remember that recognition is temporal. The significance is in the moment and then fades quickly as work and career move forward. And in sales, in particular, the scoreboard always resets back to zero soon after the recognition is received. Those trips, I remember some of the details, but most have faded into the mist. The plaques and the crystal? Dust collectors that I long ago removed as part of a spring cleaning project. What does remain? (Hint: See Knowledge and Relationships).


When I think about work and learning, I turn to the words of Mahatma Gandhi imploring us to “Live as if you were to die tomorrow. Learn as if you were to live forever.” Knowledge acquired through formal post-secondary education is vital for your career. It must be because virtually every job posting requires some level of a college education! But I maintain that real learning begins when the work starts. Money evaporates, titles are tied only to the position held, and recognition fades over time. But no one can take away the knowledge you learn throughout your career.

The Pirate’s Perspective: Knowledge is a form of currency for your life. It is one thing you can take with you from one job to the next along your career path. And take it from this old sales rep, you can also carry what you learn over your career into a successful retirement. Knowledge may be challenging to acquire, but it travels well! Whether it is hard skills or soft skills, they both matter in equal measure. A thirst for continuous learning is a highly sought-after trait in today’s job market. Show that prospective employer that you do not settle for standing still. You are always learning, adapting, and improving.


When I retired, my team presented me with a framed poster of many of my favorite Monty Python quotes. It hangs in my office for two reasons. First, I am inspired to start my day reading, “You can't have egg, bacon, Spam, and sausage without the Spam.” Second, and more importantly for me, it is a daily reminder of the relationships formed over the years working together. I say “relationships,” but what I really mean is friendship. Much is written about the importance of cultivating a professional network for your job search and your career. Not enough is written about the value of the friendships you can (and should) develop throughout your career.

The Pirate’s Perspective: By definition, working in sales for several decades, I met many people and built a large number of professional relationships. Even better, and fortunately for me, many of those business and work relationships grew into friendships that I cherish to this day. Tell me that I have to go to a desert island and take only one thing from my career with me. Hands down, I am taking the friendships established over the years. Time will take away the money, titles, and recognition. Perhaps the slow degeneration of brain cells may take away the learning. But nothing will ever replace the relationships you can build over your career.

And in the words of Jimmy Buffett, I will close by saying:

But I got stop wishing, got to go fishing,
down to rock bottom again.
Just a few friends, just a few friends.

If you like getting your job search advice served up with an authentic voice, a dose of humility, and some popular culture, please subscribe to my AdvantEdge blog.

Dan Troup is the Managing Director of the AdvantEdge Careers coaching service. If you are interested in learning more about how a job search expert and certified career coach can assist you, please contact AdvantEdge Careers for a free initial consultation.


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