If I could tell my younger self what matters in professional life…I would tell him this.

I walked out of college a free man, but I didn’t know it.  I may have been a free man with a limp and a headache thanks to a few too many days on the football field, but I was free.

I had no money to speak of and drove my girlfriend’s car. Luckily, I now know, I also had no debt. Along with that, I think I had a healthy appreciation for hard work.

Still there are a lot of things I wish I had known at that age as they relate to business and executive life.  There are things you just don’t learn in school, and many of them relate to interpersonal or even personality-based observations. That’s why I’m writing this. I figured that I can put out a few points that I wish I had known at 23, and I figure they might help someone else along the way.

One thing is for sure, they will help you understand my professional worldview.  If you read this blog, you know that it’s about worldview, and these points represent scar tissue; none of them has been fatal (totally), and some of them represent processes that have made me the professional I am.  Read them, and then tell me where I’m wrong (or right).

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Dear 23-year-old self:

You are about to embark on a career.  It’s going to be fun, frustrating, and probably not as fast-moving as you would like, so I’m going to list a few suggestions here that will give you a leg up in your career, and perhaps in your life.  Many of them you won’t be able to understand until you’ve experienced the situations themselves, and that’s just life, but some of them might help you be better prepared for the situation.

1. Invest the time on your own or in a class to learn principles of accounting and finance cold.  I know it’s an odd “reflection” to start with on a list like this one, but it’s true. Sure, your liberal arts education is valuable because it helps you to think…Sure, whatever.  But what’s really valuable is knowing how to assess organizations’ financial health, understand the time value of money, and peer into how decisions are made vs. how they should be made based on the numbers. No matter where you sit, knowing the numbers gives you a leg up, so you need the tools to learn how to know the numbers.  If you don’t know what a T-account is or can’t explain why a company would invest in a project that will lose money for five years, you need to go back to school.
2. Acquire a healthy skepticism for title and wealth. These are not always an indication of the quality of person you are dealing with.  Like British accents, titles and wealth can lead you to a false sense of security that the person you’re working with is smart and accomplished, and that is in fact often the case, but not always, and the same goes for degrees and credentials–the guy with the engineering degree from State can often run circles around the Harvard MBA.
3. Beware anyone who thinks work hours are defined by the calendar.  “My” holidays and “my” vacation are signs of a paycheck player.  If you’re on a professional track, opportunity comes at all times in all shapes.  That guy who calls you at 9 pm on a Friday?  He probably has something important to say.  I once had a manager answer the phone in Europe at 2 am local time when I called from the U.S.  I had no idea where he was, and he made no protest during the call.  I didn’t find out until later that week, after he had returned to the U.S., that he had even been in Europe when I called. I asked him why he answered, and you know his response?  “Might have been important.”  I love that guy.
4. Working harder than other people does not guarantee you success or wealth.  It might provide you with some dignity, however.  Remember Boxer from Animal Farm?  He was the noble horse who always worked hard for the cause, no matter the direction.  The work didn’t take away from his nobility, but it did kill him–he literally worked himself to death.
5. Learn and understand the snowdrift problem in game theory.  This one is kind of nerdy, but it’s real everywhere. There will always be people whose first move in a tough situation will be to wait for somebody else to do the hard work.  Be sure that you think about accountability carefully, and if you’re always the one shoveling snow, be bold enough to get out.
6. Recognize that there are people without consciences, and they are probably better at the political game than you.  I once observed an executive execute the most deceptive game of bait and switch I’ve ever seen, and shortly after that, he offered advice and support to the person who had been baited.  The kicker?  The executive knew he was being deceptive–he offered his advice with the phrase “I don’t know why you would trust us, but here’s the advice.”  The nerve.
7. Find a way to serve.
8. Learn to manage for the short term, but get out of any situation that manages to only be short term, because your life will (hopefully) be long. It’s important to learn how to manage for the short term–to cut costs and rein in spending or maybe seek additional sales to cover a shortfall elsewhere. And it’s okay to manage to the short term–that’s where we all eat.  But it’s also important to realize that just as alcoholism is the diseased extreme of enjoying a good drink, short-termism is both a disease and a kind of addiction: The more you do it, the more it becomes insidious.
9. Hotheads aren’t always bad.  I had a boss early in my career who was the greatest guy to ever throw his keyboard across a room; he was a tantrum machine, but he was also a guy who genuinely cared.  Know the difference between a grade-A jerk or asshole and a good person with a strong sense of duty but also a temper.  There is a difference.
10. Where there’s no contract, there’s no contract.  Here’s a piece of advice that’s going to sound more cynical than it is.  No, I’m not saying “always have a contract”; I’ve negotiated multi-million dollar consulting engagements that were founded on the client’s trust and the consultant’s commitment to excellence, and I believe in the power of a person’s word and handshake. But, and this is an important but, many people like to use the ambiguity of no contract to gain advantage.  So my advice to you is to always know when there is no contract–know your counterparty/client/customer, and your boss (see what I did with that last one?), as well as you know yourself.  Don’t rely on contracts, but know when you don’t have one; no amount of flattery and gushy feelings at the start of a relationship will overcome the poor values of a counterparty who won’t define or fulfill commitments.
11. Beware anyone who goes out of their way to say they are giving you friendly advice.  They probably are neither giving you advice nor being your friend.  True friends don’t have to reiterate the point; you know them by their deeds.
12. Liquid net worth provides flexibility. Whether you’re a shop floor worker or a CEO, money is important, but it’s really liquid net worth that matters; I know plenty of senior executives who are miserable but completely locked down to a bad team, bad company, or bad leader due to their own financial choices.  Always keep enough liquidity on hand to be able to walk away without regret; that means you should accumulate a few thousand bucks when you’re just out of college, and it might mean hundreds of thousands of dollars once you’ve “made it.”  Financial handcuffs are tough, which brings me to my next point…
13. People make really bad decisions when they’re under financial stress.  This can include executives cooking the books (or even “just” shading them surreptitiously) to make their bonuses, but it can also include things as innocuous as salespeople treating customers poorly or manufacturing workers doing their jobs poorly.  You really don’t want to have a workforce that’s worried about whether they can make their next grocery bill, and more than that, you don’t want a CFO who will make rotten financial and personnel decisions just to make a bonus.  The love of money is the root of all sorts of bad things–I read that somewhere.
14. Care.  Yes, I mean that: Care.  You will be tempted (in fact, encouraged in some environments) to acquire social and emotional distance from the people some think you will have to hurt to be successful; it will come with the challenge to “do what it takes” to keep your job.  But don’t be fooled–care.  I was once offered a role that implicitly came with the need to fire a couple of people I had coached and mentored and whose capabilities were strong. It wasn’t the right thing to do, so I didn’t; I chose to leave.  On the way out, I was goosed with a comment and critique about not doing what it takes, but that’s just a consequence of caring.  You know what else is a consequence of caring?  Loyalty, love, the ability to sleep well at night.  In short, your life will be better because you took the time to care.
15. Trust is cumulative…in both directions.  You will live life with a sense of trust in people you know you can rely on, but you have to learn to know when you have enough evidence to know you can trust someone, and also to know when you can’t. 
16. Respect the dignity of other people.  There are a lot of instances in life when it’s easier to double cross, lie, shade the truth, and walk away–resist that temptation. Stripped bare, we all rely on others. So respect that, and you’ll go a long way.
17. Life and business are not zero-sum games. You’ve made it through college, and maybe played some sports.  If so, you’ve gotten used to winners and losers, but life isn’t like that.  In life, there are winners of all sorts and losers of all sorts, and sometimes there are situations when everyone is a winner (or at least not losers).  Really effective executives I know think about when they are playing a zero-sum game and when they have the opportunity to grow the pie, so learn to realize the beauty of growing the pie.   Zero-sum games are in actuality very rare–we only make them common. On a related note,
18. A spreadsheet can’t show you how to grow the pie.  Unfortunately, math without vision only leads to reductive incrementalism.  Very, very few spreadsheets would have predicted the rise of Standard Oil, the emergence of digital music, or the turnaround of Apple Computer. Numbers don’t lie, but they don’t think either. Vision has to be injected into that spreadsheet; don’t mistake tools and math for strategic vision.
19. When it comes to people, where they (and you) stand depends on where they sit.  Upton Sinclair famously noted that it is difficult to get a man to understand something when his livelihood depends on his not understanding it. Perspective matters, and if you get good at taking different perspectives, you’ll start to understand how other people think, although it does take time and practice.  By altering where you sit and then thinking about where you stand, you start to think interesting thoughts when it comes to business strategy.  Funny thing is, you also start to think differently about the world.  Perhaps John D. Rockefeller (of Standard Oil) really did save the whales; perhaps Steve Jobs is actually the cause of a generation of hearing loss and an epidemic of traffic fatalities; and perhaps, just perhaps, what you’re being paid to do isn’t good for the organization or the world.  Get beyond your salary when it comes to what right and wrong look like. Stretch your thinking, and be bigger than your smallness.
20. No matter how much garbage they eat, seagulls are not really good creatures to have around. Seagulls fly in, beg for food, take a dump, and then cackle a lot; some people are enamored with them, but in reality, they’re just rats with wings (as we used to say back home on the Gulf Coast).  Seagulls live at the beach and the dump, and in human form, they often live in corporate environments.  My advice for you is to learn to be a problem solver, not a problem finder; cultivate a constructive approach to life, not just an observational one. Justify your existence, and don’t be a seagull.
21. Know how to incrementally assess situations.  The incidence of “good from far, but far from good” in people and companies is increasing because the channels of communication are increasing; it’s far easier for companies to cultivate high-profile brands that cover up lowlife cultures.  On the flip side, it’s far easier for motivated individuals to learn a lot about any situation in a short time frame. Learn to assess situations at first glance, after a few minutes, after a few days, and after months.  Learn to take the time to sleep on decisions, and do your due diligence, but also trust your gut.  This is especially true about people: If people look and smell unethical even though they’re wearing ethics as a badge, disregard the badge and go with look and feel.
22. Don’t be a “yes” man, but realize that being a “no” man is just as bad.  Yes men are common in any culture; they go along to get along.  It’s a fact of life, but not a very edifying existence, so find a way to have your own point of view or else you’ll be redundant.  But the opposite position is equally bad; the “no” man rarely encourages growth or expansion.  Try to think about growth as coming from a combination of yesses and nos, and live in the mess between the absolutes.
23. Be exceptionally careful about “following orders.”  Just following orders can give you a mental freedom that allows you to ignore basic ethical principles, and ultimately it can corrupt your values.  Have the self-respect to reflect on orders, and recognize that they shouldn’t supersede your humanity.
24. Your network is everything, but you have to know what a network is.  A real network is not the number of people you’re connected to–it’s the number of people who will do something for you if you’re in need, and there is a huge difference between the two. In my early days, people thought networking was collecting business cards; nowadays it’s probably LinkedIn connections–but both are wrong. Networking is finding reciprocal relationships that help you by your helping others.
25. If you’ve made it this far, you probably already know this, but reading is a highly underrated skill.  I’d argue it’s second only to listening.
26. Finally, and perhaps as a wrapper…Preserve your self-respect.  There will be plenty of times in your career when you’ll be faced with choices that can erode your self-respect; sometimes it’s just as simple as taking a call in the middle of a family event, and sometimes it’s worse. You’ll find months of your career that are bad for your health–it is going to happen. But even if one day you find that you have to make a choice you know is wrong but you have to do it to preserve a broader agenda or position, just be sure you know the stakes.

I’m sure you’re off to a fantastic career.  Enjoy it, and maybe one of these points will save you from a scar or two.

Sincerely,

Your much older self