Photo: “The Pen and Inkwell” by Jonathan Lhoir.
Three years ago I published 12 Career Lessons which has remained among the three most read pieces. Today, three years later in workplace altered by Covid, anticipating the impact of AI, and roiled by new mindsets whether they be of generational differences, a rise of a multi-polar world or a breakdown of trust in many institutions around the world, I am republishing the piece which has stood the test of time and change with some additional learnings and refinements to reflect the past 1000 days.
Photo: "Dawn's Whispers: Graceful Hoopoe Silhouette at Sunrise" by Hermis Valiyandiyil
The Early Years.
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 are amongst the lowest of the low and 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.
In person interaction is critical in the early years of a career for three key reasons: a) it is hard to learn how to enhance communication skills , build interpersonal skills and relationships or imbibe and adjust to to a culture remotely. These skills will be key for decades and they are easier and important to learn earlier. While it may be more expensive, less convenient and often difficult to commute and sit in a space which is not personalized the one era where in person work is key is early in ones career. Ask anyone who tried to onboard during Covid.
Early on a career my advice is to seize the opportunity that appears and build from it. Raise your hand to new opportunities. Do not say no to new experiences or difficult work because till you try it you will not know for yourself what you might learn or how you might fit.
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.
When joining a company investigate how it will be impacted in a world where AI will be embedded everywhere changing every job and new ways of communicating like AR/VR and XR create both new ways of communicating and break down barriers. How are the moats and bridges of the company and industry going to be impacted? A simple question to ask your prospect company is how they define their competitive set. If they define it with only existing competitors be careful since most industries are likely to be disrupted from outside their categories and this is an indication of management teams fixated on today or yesterday which will not work for you since most of your career will be spent in the future.
Another great question is to ask your interviewer is how they are learning or experimenting with AI or some new technology or what did they learn or build or create in the past quarter? You want to work for builders, growers, innovators, and learners and keep away from allocators, managers, delegators or monitors.
3.Plan and make decisions over a long horizon: Today 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. And even if you do not have to work for financial reasons you will do for reasons of meaning, connection and growth. Thus, do not make job or career decisions with three to five-month horizons but three to five-year horizons. Do not switch jobs just because of money unless you are under extreme financial stress. 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 questioning three days out of ten 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 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 increased resolve. 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. And with today’s health, economic and social challenges, one often longs for a pause or rewind button.
5. Compete against yourself rather than with others: The trick is not to try to better than everyone, 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 via bamboozling and sleight of hand, but you cannot really fool yourself. Get better because in it there is reward.
The goal is growth. Growth in your skills both mental and emotional. A little better every day or week compounds like interest to amazing returns particularly in the back half of your career. Build the ability to make decisions, to understand and empathize with others, to remain resilient and find ways to resurrect after a bad interlude at work. Bad stuff happens to everyone. The key is how to turn it into fuel to bounce back. Learn self-repair. Practice resurrection.
One key to growth is to spend at least an hour a day learning. If you do not have the time you are accepting obsolescence. You must find the time and with the exception of sleep and time with family and possibly exercise it is the most important investment in your life. Look around you and you will find the best in the world remain the best in the world by constantly upgrading themselves regardless of how busy or pressured they are.
Today there is even less excuse not to learn. You can access the very same AI tools as the worlds biggest firms by paying about 50 dollars a month ( GPT-4, Runway ML, Mid-Journey, Eleven Labs or their equivalents), get access to the best minds and training for free on You-Tube, Substack or podcast platforms like Spotify. The obstacles to enhancement are no longer physical or financial and if you do not seize them do remember others are…
6. Plan your career as if you were a company of one.
Think of yourself as a better paid Uber driver with benefits if you work for a company. If your expertise is needed at that time or in a particular market and location, and your collaboration and ability to work in teams is highly rated you will be in demand. If not, as companies manage and monitor costs and increasingly find ways to plug into resources all the time everywhere you will find yourself parked permanently.
The world we will be living in will be one that is driven by cloud computing, 5g speeds, AI machine learning and the death of distance is both enabling opportunities but also raising competition.
Think of the Hollywood model where expertise comes together on tv or movie projects and then the people disband and move on. Very few people work at a Studio. Most people work in teams where they bring their skill whether it be casting, directing, catering or make up etc. The future of business will be similar as companies begin re-aggregating expertise around projects versus having hordes of generalists or people hanging around for a project. McKinsey and Bain have done this for years.
I am not suggesting that everyone will be a freelancer going from gig to gig but if you build your career with the mindset of continually honing expertise, working well with other people in teams and being flexible you will succeed in your company of tens of thousands versus thinking of yourself as a cog in big machine waiting for someone to care for or build your career.
Most importantly you are the Human Resources Head of your company of one. Human Resources and Talent teams at companies including the one you work for are very important and essential to both the companies and to you BUT it is YOU and not THEY who are responsible for your career. They may be guides and resources to help you drive your career forward but you must take the wheel and steer. It is up to you with input from others to understand the map of the future terrain of the workplace and what upgrades to your driving skills or car(eer) you need and then find ways to navigate and fund what you need.
"Paper Nautilus Rider" by Renee Capozzola.
The Middle Decades.
7. 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 found people who mentored, challenged and looked after them.
Today when more people work by themselves or in small companies or move around every three of four years these mentors may be found outside ones companies including ex Clients, former bosses or other mentors. Build a kitchen cabinet or a personal board because often we ourselves are so inside ourselves that we may not see things clearly or get too high or too low on ourselves.
8. 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’ minds 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. Pursuing the highest rungs, the largest paycheck and the most external acclaim may lead you to follow the wrong star home. So many people price themselves out of their dreams and fail to recognize that Plan B was the real plan.
And sometimes it is important to stick to plan A especially if it is off the beaten path. If someone decides to work as a doctor or an engineer or a big firm they are rarely told to have a plan B. But if someone wants to be a writer, artist, creator, entrepreneur they are told to have a plan B. Plan A’s often are the best plans and if you can avoid having a cost structure that forces you to a Plan B stick to Plan A as long as you can.
The key is to maximize your options not your possessions.
9. Build your 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
Your resume is not what is on your hard drive or LinkedIn. Rather, in large part it is your web presence, particularly the first page that people see on Google when they search for you or today the answer a Chatbot provides when you ask …Who is X? Go right now and check out the responses when you put your name into a chatbot or into Google. Go look at news. Go look at pictures. Go look at videos. This is you as the future becomes more distributed and digital.
To help create a better presence think of being active on some combination of Threads, X, Instagram, TikTok or LinkedIn. Develop a website (using Square Space or some other service) think of writing a blog on some passion or hobby or even start a newsletter. Consider now of using some GPT tools to create a GPTYou. ( stay tuned for one coming from me in the next few weeks)
Photo: "The Sad Poncho" by XJ Toh.
The Later Years.
10. Unlearn. Transform. Re-Invent: Three decades plus into work still leave a decade or two of career ahead and this is where things can get really dangerous or fulfilling.
If you have been successful you might be getting 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.
Which is why has 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 have become students and learners again. 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 of trust and ensure that you do not fail since they recall the days you helped them. Sooner or later you will sow the seeds you planted and Karma is real.
For many folks the later years within a firm or outside it are often the best since they have all the mastery and fewer and fewer of the constraints. At this stage the best folks become artists. Think of late Monet with his Water Lilies which are a play on light and water that only a master could achieve or Beethoven’s late String Quartets or anything from a later Picasso.
11. Exits are as important as Entrances in Career Management: Many career books focus on impactful beginnings. There is a “first 100-day” mindset. There are many perspectives on how to fit into and make your mark into the new organization you are joining. But, there is not enough emphasis on recognizing that in multi-decade career there will be many exits. Some forced upon us (hopefully few to none) and some initiated by us. The exits at the end of a good run are particularly fraught.
A few years ago, a very successful person said “Every career has a midnight hour. The smart people leave at five to twelve”. But few do. People overstay their welcome and the end is “icky”. These endings sour the culture and tarnish an otherwise great run. The trick is to leave when they still are eager to have you around and your skills are sharp as ever.
Try not to cut ties with the companies you work for but to untie gently or when possible find to remain connected with different threads. As populations age and decline, the opportunity to leave while remaining connected will grow more prevalent.
12. 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 have been blessed with luck. They have been given chances and now is the time to give those chances back.
During the last decade keeping in mind that you need to exit on your terms, 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.
To access all my writing on Careers look at section 10 ( Managing Careers) here: https://rishadtobaccowala.com/100
Thank you for sharing your valuable and helpful insights on career planning. I continue to share them with my colleagues, friends and mentees. Happy Thanksgiving.
Filled with so many pearls of wisdom. Appreciate you sharing these insights