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Ten Career Lessons


Often when asked for career advice from students coming out of school or individuals early in their own careers here is what I share.

A. The First Decade

1. Find the least sucky job you can: Early on in your career your initial assignments being those of the starter variety will be filled with a certain rote drudgery as you being the lowest of the low will be delegated work that no one wants to do themselves.

Do not delude yourself that in your early years that you are going to find “your purpose”, “your passion” or “your identity”. Nope. You have found yourself a job in a competitive landscape and you will be learning valuable lessons on showing up even if you do not feel like coming to work to do stuff “beneath you” , how to deal with a spectrum of characters and personalities, how to present and write, and what it feels like to being bossed around.

These elementary skills will turn out to be essential in that communication skills, empathy and discipline will carry you far and be your friends forever even if you constantly change industries or the world changes around you.

Unreal expectations must be controlled in the early years or you will be seen as a sniffling blow hard in need of attitude adjustment.

2. The Trend is your Friend: If you are fortunate to be able to pick between jobs or find demand for your skills that allow you to choose between opportunities in a company do not select the higher paying one but the one that is aligned with the future. Shakespeare wrote “we must take the current when it serves. Or lose our ventures” which in modern vernacular is “go with the flow my friend”. A majority of career success is to be aligned with trends and industries that are rising and even mediocre players can succeed in an unstoppable tide. Aligning with a trend and particularly aligning early is critical because not only will the force be with you but your skills will be in demand as the area grows and if you have joined early you will be experienced and become well known in the field.

3.Plan and make decisions over a long horizon: Most people coming out of school and early in their careers will work for nearly 50 years. With life expectancies nearing the mid eighties, social security being pushed back and health holding out till the seventies it is unlikely that you will be parked on a beach in your mid fifties. Maybe in your mid sixties or later. Thus do not make job or career decisions with three to five month horizons but  three to five year horizons. Try to give each company  or assignment or adventure at least three years and if it is an industry or company at least five. Your decision making will be better, your skills will mature and you will take daily and weekly gyrations in perspective.

4. Even the best jobs are only good seventy percent of the time: If you have a great job you will find yourself wondering three days out ten you what you are doing, why you are doing it and if you are any good. The reasons for this are three fold. First. do recognize that you are being paid for what you do and the more you are paid often the harder the job is and the problems and troubles you must deal with. Often the challenges or the situations or the people you have to deal with require you to steel yourself with a drink or more. Second, if you have a great job it is one that is growing you and sometimes throws you challenges that require you to build new muscles and do new things. Learning is never easy and if you are growing there will be days that the pain will feel more like a signal that you dislike your job rather than you are building new expertise. The best jobs have flow which is a combination of competence and challenge and sometimes the challenge can be quite daunting. Finally, we are all living in a time of great change,  chaos and velocity which is filled with uncertainty . The most relevant and most transformative industries are in the eye of the storm and this can make a day at work feel like a day in the high speed spin cycle of a laundry machine.

5. Compete against yourself rather than with others: The trick is not to try to better than every one else which is neither possible nor attainable for long or with everybody who is doing the grading. Rather it is to be better every day than you were yesterday. Perpetual improvement by learning from those you admire and respect or expertise you appreciate is not only fulfilling but one that you can control free of petty politics or pissing of people that you will need to work with. Oddly it is more competitive than external competition because you can win externally often by bamboozling and sleigh of hand but you cannot really fool yourself. Get better because in it there is reward.

The Middle Years

6. Who you work for is critical so choose your boss well:  Once you get past the first decade of your career and you have learnt essential skills including how to keep learning, built an early reputation and if lucky aligned with a growing trend, the key to success is to find and hold on to the right boss. Over the next decade or two who you work for will be the determining factor in your success more than anything else you do. The middle years are really about being given new opportunities to learn and grow and linking with someone who is both growing themselves and is mentoring your own growth. A successful boss increases their remit and thus makes new opportunities for you, but also ensures that they have your back while being very upfront and straightforward with you face to face. They challenge you but cover for you when necessary. Find one or more of these and hold on tight. It makes all the difference and every successful leader has been fortunate to have someone who mentored, challenged and looked after them.

7. Find Fit: In your middle career you should begin to specialize. You now know what you enjoy and are passionate about. You also know where you have comparative advantage. And you can see where there are growing and declining opportunities. Continuously adapt your job and find ways to start doing more and more things at the intersection of passion, comparative advantage and market demand. Today, more than ever before it is experts who love their jobs that are happiest and successful. Stop thinking that everyone can or should be a CEO. And for a lot of people the CEO job makes zero sense. Stop doing and pursuing things just because other people think they are cool jobs. Stop living in other peoples mind and start living in your  own life. It is only then that autonomy, purpose and mastery come together and you fit your role and your role fits you.

8. Build a  Personal Brand: As you get to the last third of your career it is very crucial to enter it with a stellar reputation. As Jeff Bezos said a brand is what they say about you when you are not in the room. In addition to being generous and working with integrity which are key to being a successful brand it is important to be well positioned niche (what are you world class at or what is your special expertise?), have a distinct and clear voice (who are you and what do you stand for) and have a story (why should people believe you). Here is an exercise on how to build a personal brand

The Later Years

9. Unlearn. Transform. Re-Invent: A quarter of  century or three decades into work still leave a decade or more of career ahead and this is where things can get really dangerous or interesting.

If you have been successful you are  being set up for a fall because without you knowing it the Industry you grew up in is being transformed and there are new technologies and approaches that make what you learned obsolete and just when you think you have arrived you have to unlearn what made you successful.  Now you have to start learning and changing and making mistakes that you long thought you no longer have to do since you are a leader and not a rookie. You are too cool and too senior to actually make a fool of yourself but if you do not want to become as irrelevant as you fear privately  you will have to change.. Now all this talk about “change is good”that you have been stating to your teams has to be applied to yourself and you begin to realize that change actually sucks since you have to learn and trip and re-grow.

The really successful folks in the last third of the career are students and learners again and if they have built a brand and have worked with integrity and helped others along the way, a swarm of people come to help them adjust. They reverse mentor, form a trampoline and ensure that you do not fail since they recall the days you helped them.

10. Build a portfolio career and start giving back aggressively : Anyone successful in addition to working hard and playing the long game has been helped immensely by other people and of course been blessed with luck. They have been given chances and now is the time to give those chances back.

In addition it is time to build a portfolio career that expands from a job to one that includes a job, consulting, advising and giving back. Sooner or later the job will end but meaningful and purposeful work will continue. Successful older people end up being consultants part of the time and serve in advisory roles on boards or as mentors and they start teaching and helping non- profits. The folks who have ended their jobs most gracefully began these alternate streams during their last decade at work by volunteering, by teaching classes by mentoring and advising younger folks. This way they have a new road ahead when their full time job ends and because they do they move on gracefully into a new phase.

Rishad Tobaccowala is the author of “Restoring the Soul of Business: Staying Human in the Age of Data”which was published in January 2020 by Harper Collins and is available globally on Amazon and in stores.

13 comments on “Ten Career Lessons

  1. Susan Wayne says:

    Rishad – great article! i couldn’t agree more with your counsel contained here! The only thing i’d add – based on my personal experience – is be open to synchronicities and things that unfold. Don’t get attached to things turning out in any specific way. Be willing to flow with what emerges. (it’s part having a game plan and part being willing to take an unexpected turn). I hope you are well! Susan

  2. Dale Hruby says:

    Excellent advice Rishad. I plan to share this with my network of friends. Take care friend. Dale

  3. Jordan Goebel says:

    Thank you! This is great. Will share with my girlfriend and little sister.

  4. Mark Cassidy says:

    Really great article – I am always reviewing my own marketing plan and this is dead on!

  5. Mike Rezac says:

    Wonderful article. It describes what many of us are considering or experiencing in our careers.
    A key is to always keep learning…or “unlearn” as you have accurately stated.

    I will be sharing.

  6. Rick Roth says:

    Love this! Thanks Rishad. Wise perspective for all ages.

  7. Cheryl Riley says:

    This article describes what many of us are going or have gone through. Good points! I shared with a few people that are just beginning their careers that have expressed their feelings to what you list to expect. It always helps to know that you are not alone in the way you feel and to receive advice what you can expect.

  8. Jack Phifer says:

    Really exceptional perspective, I couldn’t agree more!

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