I’m having a really hard time thinking today. The reason is personal, and I really don’t want to get into it here and bum you out too. It’s just one of those days. We all have them.

On a more optimistic note, … Wait. On second thought, forget that. Optimism is so overrated. There’s nothing more annoying and reckless than someone who fakes positivity he’s not feeling or hopefulness that isn’t justified. Now I’m all out of synonyms for optimism.

Truth is, I’ve built my entire career on telling it like it is, good news or bad. Business is business, not a popularity contest. Work is work, not a lovefest. You always want to reach the right conclusions and make good decisions, even if they’re unpopular. And the only way I know to do that is to search for truth and question the status quo.

And if your instincts tell you that it’s time to be concerned or worried, don’t sweep that under a rug of happy thoughts and grinning emojis. Trust your feelings. And communicate them to those who depend on you.

I’ve always heard that Tim Draper – a legendary venture capitalist in the Valley – is the most optimistic guy around. He’s always positive. No wonder. He’s a third generation VC who grew up in an elite family: a long line of rich ivy league grads who spent their lives hobnobbing with America’s wealthiest political and business leaders. What does he have to be down about?

OK, I know that sounds cynical. Just my mood du jour, I guess.

More important, if Draper’s unflappable optimism made him sing the praises of Elizabeth Holmes long after it was evident that her company, Theranos, had achieved a $9 billion valuation by defrauding investors, customers and partners, not to mention by selling thousands of patients inaccurate blood test results, then please, call me a proud pessimist.

Actually, I’m not a pessimist; I’m a realist. I know, I know; that’s what optimists say pessimists call themselves. Maybe there is some truth to that. All I know is, my career has always come down to three things: results, relationships and reputation. Executives and business leaders get paid for being right, not for blowing smoke up people’s behinds.

Actually, let me rephrase that: not from blowing smoke up the behinds of those who matter. Let the shyster gurus of the world sell their souls for a buck and sell the masses all the fluffy BS they want to hear all day long. That’s not for you and me. If it is, you’re definitely reading the wrong blog.

Don’t get me wrong. I’m not saying it’s a good idea to walk around the workplace whining about this and that and bringing everyone down. You can be genuine without being a bummer.

A big part of being a good leader, boss, coworker, spouse or friend is being aware of what’s going on around you and choosing the right time and place to say things. And trust me when I tell you, some things have no right time and place. Some things are better left unsaid. Probably most things. You know what I’m talking about.

So hey, if you’re an optimist, be an optimist. If you’re a pessimist, be a pessimist. If you’re the next Machiavelli realist, so be it. And if you’re a pessimist who calls herself a realist, that’s OK too. Just as long as it’s true. Just as long as you’re really feeling it. Just as long as it’s the real you.

  • BigGameHunter

    Good post, Steve. That concept of realism made me recall a line from The Godfather. This was the scene where Robert Duvall was sitting across the dinner table from the Hollywood film producer who had just said “no” to the idea of Johnny Fontane starring in an upcoming film at The Don’s request. Upon hearing that answer, Duvall wiped his mouth with his napkin, thanked the producer for his hospitality, and said he must return to New York because “one thing Don Corleone insists on is hearing bad news immediately”. Bad news has a habit of hiding in the shadows in the corporate world. It also happens to be where I went to “business school”. Somewhere between optimism and pessimism is realism, and I ended up defining realism as truth. Employees, colleagues, investors, markets and families desperately seek truth in ALL things today. And once they get the truth, I guess they can decide whether to be optimistic or pessimistic about it.

    On another note, a dear friend bought me your book. I was remiss in getting it for every excuse in the world. I am enjoying it to the hilt, and encourage others to get it.

    • Steve Tobak

      Guess we went to the same biz school. Thanks re: Real Leaders. About freakin’ time, buddy. 😉

      • BigGameHunter

        For sure. Can I at least say it was worth the wait? All kidding aside, it’s a gem of a book.

  • Danny

    Very well said! One of your best pieces. Some very horrible news was reported this week regarding the significant rise in teen suicide rate. Teens do not hear it enough that it is ok to be themselves, the real them, and taught how to love who they are and how to get their identity the right way instead of the cultural ‘fake it until they make it’. Whatever “make it” is for them. Steve you really need to think of how you can get your body of work in front of high school and college age kids, because it represents, IMO, a great message they need to hear. My daughter is a college professor, and I had her start reading your blog, and have suggested she share some of the topics with her students, and she does. I have recommended your book and blog to business people I know, but I’m old so they are people at the peek of their careers or retired. It is the young folks who you need to reach, to displace the garage they are being fed.

    • Steve Tobak

      You’re right, Danny. After all, Real Leaders Don’t Follow was dedicated: “For tomorrow’s business leaders.” Your and everyone else’s efforts to spread the word are very much appreciated.

  • My definition of an “optimist” (borne of personal experience) — “A musician with a mortgage.”

    Back when I was gigging for a “living,” my wife’s joke was that her husband “is in the non-profit sector.”

    • BigGameHunter

      This absolutely cracked me up, BobbyG. You also made three others who appreciate gigging laugh out loud. Best wishes to you in all you do going forward.

  • Anurodh Sharma

    Thanks Steve, my take is be yourself, whatever you are…..REALLY!!!!