100 Things This CEO Wishes Someone Had Told Him After College and Before He Entered the Real World

Today, I have the honor of addressing the 2019 Graduating Economics Class from the University of Rochester. It was a mere 36 years since I was sitting in their exact seats as a class of ’83 graduate, and I have given some reflection on the things I know today that I wish I knew the day I received my newly minted degree from the University of Rochester.

This was similar to the exercise that led me to create a list I gave to my four college-bound children that resulted in the 100 Things I Wish Someone Had Told Me Before College. I share this new list with the hope that perhaps one idea will resonate with just one graduate and it will give her or him some perspective as they begin their next phase of life’s adventure.

University of Rochester Rush Rhees library

Wishing all graduates from every school the very best as they navigate their future,

Chairman & CEO Jefferies
Chair of the Board of Trustees, University of Rochester
@handlerrich Twitter | Instagram

100 Things I Wish Someone Had Told Me After College And Before I Entered The Real World

1. The most valuable asset you will ever have in your career is your reputation. It is also the most fragile.

2. Treat your first and every job like you are certain it is your ultimate career. First, it might be, and second, this is the only way to truly find out.

3. Petty internal politics may seem to work great in the short term. They won’t get you where you want to go in the long term.

4. A career is not a zero sum game. This is such a simple statement to make, but one of the hardest concepts to believe and live by.

5. Find a mentor. If you are fortunate to earn one, this person will challenge you beyond what you believe you are capable of achieving. They will instill within you a confidence that comes from knowing someone you respect believes in you.

This is a person you can expose your vulnerability to and receive honest (sometimes painful) constructive advice. This person will not only make a difference in your career, but will have true impact on the person you will become and the legacy you will leave.

6. A mentor doesn’t have to be the person who is most like you or who you like the most. It should be the person you can learn the most from. Sometimes this person is difficult, challenging and not fun. That’s ok because your goal is to learn and grow, not to hang out.

7. There has to be something in it for the mentor or why would anyone choose this role? A mentor will only be inspired to take on this role if they see a special spark inside you. You can’t pick your mentor. You can identify the candidates and work towards the goal, but they are the ones who get to pick.

8. Not surprisingly everyone wants a mentor and sadly very few people want a mentee. Why should a mentor want you if you are not the kind of person who chooses to give back by finding a worthy mentee?

9. You are never too junior to have a mentee. All you have to do is care about those who know less than you, but have the potential to make the world better. You may not believe it but you already have valuable experience to share. The amazing thing about life is the more people you mentor, the more you learn and the more rewarding your own life becomes. Don’t worry about having enough time. It will work out.

10. If you surround yourself with smart people, you will be challenged, uncomfortable, and grow as a person.

11. If you surround yourself with average people, you will stay very comfortably average.

12. If you surround yourself with less intelligent people, the company will fail or you will get fired.

13. It is ok to make lots of mistakes. They are usually minor and it happens every day. That is good and how you learn.

14. If you make the same mistakes over and over again, that is not good.

15. There are only a handful of giant decisions that one needs to make during their entire career. Recognize when you are at one of these big inflection points and truly reflect on the situation and assess all of the relevant facts.

Take your time to make decisions and speak with everyone you respect. It is critical to get these giant decisions right. If you are successful in getting the big decisions right, people will marvel at your long-term trajectory. If you do not succeed here, you alter an otherwise positive path and it may be very hard, if not impossible to fully recover your optimal arc.

16. Choose an employer where there is a lot of flow. Flow means smart people, many potential experiences, lots of transactions, constant buzz, too much work and not enough people to get the job done. The more you are in the middle of what may seem like an “unorganized and constant mess” of “too many things to do,” the greater the opportunity you have to gain valuable experience. The best way to learn is by doing.

17. If nobody at your new job cares about you or your future, it won’t be impossible, but it’s going to be a lot tougher to succeed. Try to surround yourself at work with at least some people who truly care about you as a human being.

18. Don’t ever go into a field or a job because others think it’s great. You have to think it’s great.

19. Independent thought is a very valuable and scarce commodity. It feels much more comfortable to go along with Groupthink and not rocking the boat. Groupthink provides a false sense of security and is seldom rewarded and often wrong. That said, don’t be a contrarian just for the sake of being a contrarian because sometimes when things appear obvious, they are. Use your brain.

20. You are not smart enough to “just wing it.” Maybe it got you this far, but you need to truly do the work if you truly want to contribute and make a difference in the real world. In case you are not aware, you are now entering the real world.

21. It’s called work for a reason. Sometimes you will be miserable. It’s ok to sometimes be miserable if you are learning, growing and striving towards something you believe in.

22. It’s very easy to say, “I am are miserable,” “the people I work with don’t get it,” or “everything about the company/industry is stupid, wrong, or broken.” Talk is cheap and complaining is easy. Try to fix what is wrong because that is how you add value. Otherwise, you are also just part of the problem.

23. Never go into your boss’s office and tell her/him what is “broken, wrong, or stupid.” Always go into your boss’s office with a plan to improve whatever is “broken, wrong or stupid.” You’re probably better off not referring to things to your boss as “broken, wrong or stupid,” but sometimes it will be impossible to help yourself. At least try to tone it down if possible.

24. If you are the kind of person who always points fingers at others, you may be the problem, and don’t be surprised that when you are out of the room, everyone else’s fingers are pointing towards you.

25. Work can and should be fun. Unless you become a brain surgeon, your job probably isn’t brain surgery or life and death. Have perspective. It’s not just ok, but it is beneficial to your career to let your personality shine and show your individuality, sense of humor, and personality. That said, unless you become a professional comedian for a living, don’t overdo it.

26. Work is not a fraternity or sorority party. If you step out of bounds publicly at work or on a business trip, it can be a career-changer. Don’t get drunk at the office holiday party. Everyone knows and talks about it and you will be labeled.

27. Work is serious. There are clients, investors, regulators, co-workers, laws etc… If you aren’t serious about your career, goof around badly outside of the office, post inappropriately on social media, or do anything that will show a lack of self-respect, you should have no doubt why your career trajectory is limited at best.

28. If you consider gender, color, race, religion, or sexual orientation to be a determining factor in anything in life, you will and should be fired.

29. If you don’t understand appropriate behavior at this point in your life, no company will be interested in taking the time to explain it to you. There are no longer three strikes. One and done. As it should be. Consider this the only warning you will ever receive.

30. You can’t ask enough questions when you want to learn. Don’t ask the same ones over and over again, and be sensitive enough to know when its’s appropriate to be inquisitive and when it’s not.

31. If you can master empathy, the art of putting yourself in other people’s shoes, you are going to have an extraordinary career.

32. If you think the world revolves around you, there will be a day of rude awakening. The institution was there before you arrived and the world will keep revolving after you are gone. Nobody is irreplaceable. Never forget this.

33. Most companies thrive by increasing revenues and reducing costs. If you can be part of helping a company grow or be more efficient, you deserve a seat at the table. If you do neither, you may want to re-evaluate exactly what you are doing. This doesn’t mean research, strategic planning, culture building, etc…isn’t super valuable. They all are. When you think about it, usually these areas are just longer term paths of increasing revenues or reducing costs, so recognize it as such.

34. It’s easy to just quit your job and feel justified. It’s a lot tougher but much more rewarding to step up and do everything in your power to improve things.

35. If you wake up in a few years and see multiple jobs on your resume, it is usually a sign that you are doing something wrong and future employers will question your judgement, loyalty and competence. You may think you can talk your way out of this, but smart interviewers from good companies will easily discover the truth. You can probably fool some mediocre interviewers from marginal companies, but eventually you will just add this new job to your prematurely long resume.

36. Sometimes you do need to quit. But only after you have done everything in your power to make things better and right. You owe this to yourself and your employer. However, if you ever see real ethics issues or fundamental core problems that are ignored by those in charge, quit immediately. Bad reputations are contagious.

37. Find something you are truly passionate about and believe in. When you do, you never once look at the clock.

38. Start with balance in your life right away. As a junior person this may seem impossible, but it isn’t. Yes, your time will be greatly skewed towards proving yourself when you begin your career, but setting aside some time to exercise, eat well, and spend time with your family and friends will provide you with at least a little balance. You do nobody any good when you burn yourself out, are constantly sick, are always bitter or lose perspective on life.

39. The single most important career decision you will ever make is to pick the right spouse/partner. If you pick the right one, you will have someone to celebrate every success, support you through every inevitable setback, and give you honest feedback along the way. If you pick the wrong partner, your life will be much harder, more lonely, overly complicated, and far less meaningful. I highly recommend, if at all possible, to get it right the first time. If you feel doubt and apprehension about the relationship, listen to yourself.

40. Celebrate your promotions. They are a big deal and a reward for a job well done.

41. Never work day-to-day with the goal being to achieve a promotion. If you come to work with the right attitude, strive to be incredibly competent, put the needs of the whole ahead of your personal agenda, always behave ethically, and do your best to make a difference, you will get promoted. This is not a coincidence. Promotion is the result of exhibiting your best behavior and actions every day and never occurs because it is you top priority.

42. Don’t freak out if someone else gets promoted and you don’t. Celebrate with them and do an honest assessment of why this happened. It might not have been the right time for you. There might be a better direction for you that someone else sees. It might be you made some mistakes along the way so this is a good wake up call to re-evaluate and pivot. It might be that you are really not happy and haven’t woken to the fact, so you have some soul searching to do.

43. Anyone can get a job. Very few can truly have a career. Know the difference.

44. Get out of your comfort zone at work. If you are really good at one area or task, do your best to explore others as well. The more breadth you have, the more valuable you become. That said, you need to get your work done first and it is great to be an expert in at least a few things.

45. Work is people. Every career starts and ends with people. If you are the smartest person in the room and can’t deal with people, how smart can you really be? Figure it out.

46. When everyone comes to you with their issues and problems, that is a very good thing. It means they believe you can help them be better at what they do. Never complain when people come to you for help. If nobody comes to you, that just means they don’t think you can add value. That may seem like a simpler, relaxing and easier way to spend your day. Unfortunately it also means that you have a job and not a career and worse yet, that job might not last much longer. It’s best to be bothered constantly by people who need your help. It means you matter.

47. If you spend your career helping others solve their problems, making everyone around you better, accepting your share of blame for setbacks, and sharing credit for the successes, don’t be surprised if you eventually find yourself with a new title: CEO.

48. Conniving people ALWAYS get caught. It may take longer than you would like, but don’t worry, they will get caught.

49. You need to own and manage your career. Even if you have a great boss, amazing mentor, or wonderful company, you need to assume full responsibility. This requires you to give yourself honest and critical feedback. What do you need to learn to be better? What relationships are important for you to better nurture? What future paths do you see as logical progressions? What is the greatest need of the company that nobody else is rolling up their sleeves to accomplish? Take ownership of your career.

50. Constantly invest in yourself. It’s not a coincidence that the people who take night classes, read constantly, understand the company or industry best, and emerge themselves fully in their opportunities are always the ones who rise to the top. It’s never luck. Losers just say it is.

51. Just because you are a junior person doesn’t mean you can’t be a remarkable spokesperson for your job, company or industry. If you are the one who is recruiting other great people to join what you are doing, you are adding value. If you are trying to keep out the best people because they are competition for you, you are destroying value. Believe in where you work and spread the word. Also believe in yourself.

52. Learn how to interview people. It is a very important and valuable skill. The first place to learn is by honestly assessing the process you just went through. Who interviewed you well and who did it poorly. Who got to know your strengths and weaknesses and who were you able to fool. What were the real questions that made you reflect and which ones were a waste of time? Which interviewer did all the blabbing and which one got you to honestly reveal yourself? There are always two sides to every interaction, but only if you realize this and pay attention.

53. Arrogance is the one trait that will destroy your career. It’s just a matter of time. The more successful you become, the more humble you should be. A humble superstar is invincible.

54. Always deliver bad news honestly, promptly, and directly. Bad news rarely gets better. If the answer is a hard “no,” an immediate “no” is far better than a long maybe which eventually is just a more awkward “no.” If you make a mistake, own it. Never deflect. If you don’t understand something, speak up. Problems never just disappear. Small issues just fester and the longer the duration, the greater the odds that they become bigger problems.

55. When you are asked to do an assignment, do exactly as asked but always allow yourself some time to step back and reflect on what the purpose and conclusion of your work truly is. It is so easy to get caught up in the weeds and go robotically from task to task. Big picture reflection will allow you to grow. If you can’t figure out why you were asked to do something or what it will be used for, find the right time and ask the right person. It will also help you do the next task better and you will enjoy it more.

56. It is good to have an idea of where you want to be in 5 or 10 years. If you know the general direction, at least you know which way to constantly lean. This ultimate destination may change over the years, but that is fine. Nothing is carved in stone but if you are happy to just be constantly adrift and go wherever the tide takes you, don’t be surprised if you end up washed up on the shore. Pick a direction and use your inner compass. You can always modify as needed.

57. The most important and successful people are easily and constantly accessible. One may wonder why very important and successful people always return every call or email promptly. The answer is that they always did, and that is how they became successful and important. People who give the illusion of being too busy and important rarely are.

58. Be proud of where you work and what you do. Wear your company hat or t-shirt. If your company has an iPhone case with the logo on the back and you don’t want to use it, you may be at the wrong company. It is ok to “buy in” and be part of something bigger than you. Be proud. Never get brainwashed.

59. Never forget that while your job/career is tremendously important, it will never define who you are as a person.

60. Always be a good person. You know what this means. If you worry that you are doing something that goes against this simple code, don’t do it.

61. Respect experience. This doesn’t mean that new initiatives, fresh ideas, and youthful exuberance aren’t the lifeblood of every company or endeavor. They are. That said, real world experience from people who themselves were also once young and perhaps overly optimistic is really valuable and important. They may be completely wrong and the world may have changed dramatically, but maybe not. Listen, do the work, respect the viewpoint, and only then decide how best to move forward.

62. Embrace every single aspect of technology possible. Today, it may appear easy given how fresh and cutting edge you know you are as a recent graduate entering the workforce. But, trust me, in 5 years (probably less) there will be new people who will be even fresher with even sharper cutting edges and only when you experience that will you be able to honestly say you are open to embracing technological change.

63. It’s more important to work smart than hard. That said, the best people do both and there are plenty of them so get to it.

64. Only go back to graduate school if you know exactly why you are going and you get into the right one to achieve your objectives.

65. Always live within your means. It’s never too early to begin your financial plan. If you are frivolous in youth, you won’t have the means to be frivolous when you are older. Trust me, It’s fun to be frivolous when you are older. Read the “The Richest Man in Babylon” by George S. Clason. It will cost you a couple of hours but you will save a couple of decades. That’s what we call a good investment. Learn about this thing your parent’s hate called taxes. They suck but they are real and better to understand early than pretend they don’t exist. Always pay them.

66. You can get trapped into a job versus a career when you prematurely take on fixed obligations that limit your ability to be flexible. This can happen and sometimes this is just life. Try to have your eyes wide open and do your best to make pro-active choices versus being forced into reactive ones when it comes to changes in flexibility. This may require more specificity so I will spell it out: I’m referring to marriage, children, real estate, other large purchases, or anything that will limit your options to be incredibly flexible. I’m not saying don’t do any of these, I’m saying ideally there is a time and a place for all. Better for you to proactively choose than to have it chosen for you.

67. Constantly write down your life goals and re-assess. It is fine if they change over time. It is not fine if you are not honest in your re-assessments.

68. There are many ways to find satisfaction in one’s career. The rewards can be monetary, psychic, intellectual, spiritual, or other. Some people are fortunate enough to have a combination. What’s most important is to pick the career that best aligns with the reward(s) that you value the most and then allow yourself to enjoy it. Never be jealous of people who picked careers with different rewards because that only serves to belittle the goals and objectives you have set for yourself. You have to know and be honest with yourself as well.

69. If you are fortunate enough to have some monetary rewards as a result of your chosen path, you have a responsibility and an obligation to share with those less financially fortunate. It is your right to pick the group of people, cause or issue to support, but you need to start as soon as possible. It is never too early and it is never about the quantum of money. To be able to give back is a privilege.

70. The best gift of philanthropy you can give is your energy, spirit and time. With 100 percent certainty, you will be the greatest beneficiary from this investment and commitment.

71. People whose jobs offer primarily psychic and spiritual rewards may wind up being the wealthiest, even though it might not seem so all the time.

72. You are now in the real world and $hit happens. For some reason, people love winners. There will be no challenge finding a best friend when you are on top of the world. It may appear a little lonelier and quieter when everything is going badly for you and you find yourself a disappointed mess. Miraculously this is the only time you will find out who are your true friends. People with character shine when they see people in need. Always surround yourself with people that have true character and rid yourself of fakes. To successfully do so, you must have true character yourself. This is one case where opposites do not attract.

73. Know your boundaries. Your boss and your boss’s boss may one day become your friend, but odds are today they are not. Don’t overstep. Don’t presume. Pay attention to cues and always be aware.

74. There is a really important concept called EQ. It is more important than IQ. People with great EQ can always hire people with high IQ. If you don’t know what EQ is, look it up.

75. If you create a lot of wealth in your career and along the way you forget who you are, you are very poor. Wealth never makes you a better person. It could make you a worse person.

76. Nobody gets wealthy because their goal was to become rich. It is always a bi-product of being passionate about working with others to create something that adds value to people’s lives.

77. It is a lot of fun to be part of building something you believe in. It could be a product, division, idea, initiative, company or industry. It doesn’t matter what it is, as long as you are empowered to be part of the building and you believe in the ultimate objective.

78. Major setbacks are the pivotal times that allow for great things to happen in the future. If you dwell on your setbacks and sink into the abyss, you’ll be doomed. However, if you embrace your setbacks, learn from them and grow, you will be unstoppable. Then people will whisper behind your back, “ why does everything always work out for you…..you are so darn lucky.” Luck helps but is rarely the determining factor.

79. If you spend one percent of your time on office/work gossip and nonsense, you will find it a very slippery slope. One percent will become ten percent and you won’t be able to stop there. It is all wasted time and only serves to reinforce to others that you are not a serious person.

80. People are either culture carriers or culture destroyers. If you have doubts about which one you are, it is probably clear to everyone else that you are part of the problem and not part of the solution.

81. Time will be your scarcest resource. Don’t waste it. The only way not to waste it is to be honest with yourself in assessing how you spend it.

82. If you think you need to show “face time” to get ahead, you either are not good enough at what you do or you are working at the wrong place. Competence, efficiency, integrity, and results matter. Unless you get a career in modeling, your face being seen is not going be the difference maker.

83. Sometimes common sense is forgotten. Don’t get yourself tied up into a knot on a complex issue with multiple angles and accidentally drift away from a solution that is actually quite simple. If in doubt, keep it simple and rely on common sense. If this is not one of your strengths, ask someone who has an extra portion of common sense what they think.

84. In today’s world, there are smart ways for companies to allow for greater flexibility to accommodate their people’s individual needs. Nobody wants to lose great people because they can’t fit into a specific work box or constraint. If you have special needs, be smart about it and don’t be afraid to speak up. If you don’t speak up, don’t expect the problem to solve itself.

Try to think the issues through and come up with a potential plan that works for everyone. Remember, you still must be productive and efficient and recognize the time constraints and demands of the people you work with must also be met.

85. Communication skills are critical. If the best ideas cannot be properly communicated, they don’t count. If you are nervous speaking in front of a group, take a speech class. Writing skill are important and can be supplemented. There is an art to writing short and succinct emails. Don’t waste people’s time and learn to always get your point across effectively.

Never “respond to all” when not needed and always understand the nuances of “bcc”. It’s better to never use “bcc” and perhaps ask yourself why you are afraid of not letting others know who you are communicating with. Might be better for all to address that issue rather than sending a message with “bcc”.

86. If you are sitting in a room and you know you have something to contribute, but that pit in your stomach tells your brain to not let your mouth open because you are too nervous, suck it up and speak your mind. Trust that you know when you have something important to contribute and force yourself to do so. It will get easier over time but you need to start. Nobody in the room will ever surmise that you had the value-added answer unless they hear it from you at the critical juncture.

87. Always be respectful of everyone but never be intimidated by anyone because of their perceived importance, experience, tenure, stature or title. People are people. Everyone was junior at one time. Most senior people have kids and they are proud to teach. Most senior people are excited when they see the next generation speak up and contribute. You are the future, but you need to show it and earn it.

88. One stupid incident and you will tarnish the brand and reputation of everyone around you. You are now responsible for everyone you work with. It is a major responsibility. It’s no longer just about you. Never forget this.

89. Today’s world is completely transparent, especially today. There are no secrets. Everyone has at least one best friend who they will tell the “super-secret” information. By the way, that friend also has one other best friend. Don’t delude yourself into a false sense of security. If you have nothing to hide, you don’t have to worry when you assume everyone knows.

90. The more senior you become, the more people you work for. Most people think it is the reverse. They don’t have a clue.

91. Everyone has self-doubt and we are all making it up as we go. You are in the real world now and there is no official game plan, curriculum, graduation date, or standardized test to let you know where you stand. Figure it out.

92. Nobody cares where you went to school or what your GPA was once you get the job. Now it’s all about what you can do today and tomorrow.

93. You will now be meeting a lot of people. There will be co-workers, fellow commuters, strangers, clients, investors, networking events and a constant barrage of new people around you. Every person you meet is an opportunity to establish a new relationship. It is impossible to immediately determine which of these interactions will be non-consequential and which will be life changing.

If you are truly sincere and open to meeting new people and getting to truly know them, your likelihood of an amazing career will skyrocket. If you are only focusing on people you perceive to be important to your immediate future, you will never make it. Clients can be found in a subway. Waiters at restaurants can be future business partners. Executives at a competing firm can wind up being your soul mate.

It is obvious when people are really tuned out to the world until they perceive an opportunity for self-advancement and then it is obvious when they push the superficial and artificial charm button. Successful people have time for everyone and are sincerely open to all, whether they are your food delivery person or a CEO. Who do you think will have a greater chance of success? Do you really think that people can’t tell the difference?

94. Pay your bills on time. Bad credit early on is a big problem. Don’t get lulled into easy credit card debt.

95. It is never too early to get into the routine of regular physicals. Healthcare costs a fortune but the alternative is worse.

96. Ask your family and friends you respect for advice. You don’t have to ultimately listen to it but it’s always best to hear from people who unequivocally have your best interest in mind. That said, when you only give them your biased side of the story and ask their opinion, they will only confirm your viewpoint and their advice will be meaningless.

97. Everyone wants to be around people who are optimistic, forward looking, have positive energy and light up the room with a smile.

98. Grooming matters.

99. It is a very long race. You will waste your life if you decide to enjoy yourself only once you cross a specific finish line.

100. Whatever you do, keep in mind that at the end of the day you have to feel proud about the people you work with, the mission you are all on, what your company and career stand for, and whether you are empowered to personally help make a difference.

Rich Handler is Chief Executive Officer and Director of Jefferies Financial Group Inc. (NYSE:JEF), parent company of Jefferies Group LLC and Chairman of the Board, Chief Executive Officer and President of Jefferies Group LLC.

Rich has been with Jefferies since 1990 and has served as Chief Executive Officer since 2001, making him the longest serving CEO on Wall Street. Prior to Jefferies he worked at Drexel Burnham Lambert in the High Yield Bond Department. Mr. Handler also serves as the Chairman and CEO of the Handler Family Foundation, a non-profit foundation that focuses on many areas, including providing all expenses paid college education each year to 15 of the most talented students coming from challenging backgrounds. The foundation also works to protect the environment by saving endangered species. Mr. Handler received an MBA from Stanford University in 1987. He received his BA in Economics (Magna Cum Laude, High Distinction) from the University of Rochester in 1983 where he also serves as Chairman of the Board of Trustees.

Follow Rich on Twitter and Instagram.

You Might Also Want to Read: 

100 Things This Wall Street CEO Wanted His Kids To Know Before They Left For College

Why You Should Help Your Kid Get a Job 

About Grown and Flown

Mary Dell Harrington and Lisa (Endlich) Heffernan are the co-founders of Grown and Flown the #1 site for parents of teens, college students and young adults, reaching millions of parents every month. They are writers (Lisa is a New York Times bestselling author), moms, wives and friends. They started the Grown and Flown Parents Facebook Group and are co-authors of Grown and Flown: How to Support Your Teen, Stay Close as a Family, and Raise Independent Adults (Flatiron Books) now in paperback.

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