A one-of-a-kind thinker with a hilarious yet considered point of view, we can all learn some practical life skills from author, speaker, pundit, and comedian Jeff Kreisler. With expertise in politics, money, and behavioral science, and an affable brand of humor that adds levity to every subject he tackles, we were eager to learn a few of his trade secrets to apply to the more frustrating or awkward workplace moments we often encounter. His latest book about mastering personal finance, co-authored with behavioral economist Dan Ariely, is titled Dollars and Sense, and is cited by Business Insider as “ …the rare kind of book that makes you feel a lot smarter, while simultaneously giving you actionable tips for improving your daily life.” We couldn’t wait to see how the Princeton-educated thought leader would tackle questions about branding, the workplace, teamwork and the bonding power of a nice glass of wine.

1. 

You’re a lawyer, an author, a political commentator, and a comedian. How do you effectively brand yourself when you’ve got so many areas of expertise? Please give branding advice for readers who are multitalented like you!

Focus on your vision. Even the most diverse career needs a guiding vision—and the ability to succinctly communicate that vision to others. Ah, but how do you define that vision, especially when you’re doing a billion things?

1.  Say no. Stop doing things you don’t want to do or aren’t good at doing. If it doesn’t add to your career, it detracts. This isn’t easy—you gotta eat—but start paring it down. 

For me, I haven’t thought of myself as a lawyer in 10 years and I don’t want any work that involves being a lawyer.  So, except as an interesting talking point and to show that I’m “smart,” that doesn’t come up. Certainly not in my brand or outreach.

2. Assess your career thematically. What unifying themes run through your work?

I’ve been inspired by politics, cheating, and the way money messes with our heads. When I break those things down further, I find common themes of exposing how we are misled into making poor decisions and explaining why. If a project touches on that theme, it’s easier to explain how my work is related.

3. Distill skills and experience into simple concepts and show how they apply in a broad range of settings. I’ve written books, TV, and speeches, and I’ve helped people at all levels become better communicators. I’ve taken complex ideas and made them accessible to a broader audience.  I’ve done a lot of research to make sure the messages I’m spreading are accurate and up to date. I’m funny.  (Present interview excepted). So I look at that, play with it, and I now say “I use humor, research and communication skills to understand, explain, and change the world.”  That’s not super-sexy cocktail party talk, but if someone’s looking to hire or partner up, it’s more info than “I’m a writer,” but not too much to understand.

4.  Which leads to a final point: make it easy for other people to get what you’re about.  Simplify, simplify, simplify. It is really awesome to have done a bunch of different things, to weave a rich tapestry of life and work. I wouldn’t trade my path for anything. But if I just listed all the things I’ve done and all the things I can do, people would scratch their heads and go, “Oh, that’s cool,” and move on.  I’ve got to make it easy for them to understand how I can help them achieve their goals and further their vision.  Then we can combine powers and rule the galaxy. Which would be cool.

“We can’t change human nature, but we can use human nature to our advantage...”

2. 

Your book with Dan Ariely, Dollars and Sense, helps people better make better sense of their financial decisions. How could your book help, say, a freelancer who is looking to increase their monthly income? Or a full-time employee who can’t seem to save any money and lives from paycheck to paycheck?

In many ways, our book is about how we incorrectly value things, whether our own economic worth or the worth of a spending decision.  So whether it’s about income or spending, saving, investments, or any other financial assessment, recognizing our mental mistakes and understanding why we make them is the first big step to changing outcomes.  We can’t change human nature, but we can use human nature to our advantage, instead of allowing marketers and hiring people alike to use human nature to take advantage of us. 

One specific example is being aware of how and why we overvalue fairness and effort.  There is a legend that Pablo Picasso was approached in the park by a woman who insisted he paint her portrait. He looked her over for a moment, then, with a single stroke, drew her a perfect portrait.

“You captured my essence with one stroke. Amazing! How much do I owe you?”

“Five thousand dollars,” Picasso replied.

“What? That’s not fair. It took no effort! It only took you a few seconds!”

“No, ma’am. It took me my entire life and a few seconds.”

Like the woman in the park, we often value things based upon the effort we see. We’ll pay more to a locksmith that fumbles around and takes an hour than one who opens our door in 30 seconds. Because it looks like it took more effort and that seems more fair to us. 

As service providers, we should be aware that those hiring us may not understand everything that goes into our work. They may only see the minute—or week or month—it takes to create something, not the lifetime of (usually unpaid) learning and growing (and marketing and selling) that goes into it. We should find ways to be more transparent about the effort and skills that go into our talent.

As consumers, we should be aware that we are prone to fall for the appearance of effort. Fancy restaurants take pains to describe how hard it was to procure and combine every ingredient of their high-priced delicacies.  Consider the $29 hamburger: maybe it’s worth it to know how hard it was to grow the type of grass eaten by what you’re eating… but probably not.  

3.

Speaking of Dan Ariely, you two seem like a bit of an odd couple. Is that true? Since you presumably spent many hours together working on the book, any advice on what makes good teamwork? 

No, we aren’t exactly alike—I like to think of myself as “half the Dan at a quarter of the price” ;)—but our differences complement each other.  He had the great information and message; I had the skills to share them in a new way. 

Most important was what we had in common: our shared vision of what the book would be, what we wanted to say, what we wanted to do. We may have differed on how we did what and when, but it all came back to a shared focus on a common goal.  And that made the bumps easier to smooth out.

Speaking of which, what makes good teamwork? Communication, communication, communication. We had good communication, even though it was a challenge because we rarely were in the same state, let alone same room. It wasn’t constant communication, but it was effective.

The main thing that Dan and I had to make sure we communicated clearly was expectations.  Knowing who is expected to do what by when—and being flexible with changing those when needed, without ego. Whether it’s about schedule or the substance of the work, being able to say you were wrong is also vital.  Having the confidence, humility, and support to then reach out to your partner and say, “You know what, this isn’t working. Here’s where we are with it. Let’s talk about what we should do next.” We tried four different approaches to writing the book before we settled on the last, best one—but we were okay with with abandoning ship and starting over. Trial and error and the support of your partner to mess up and begin again. Basically, we used the scientific method. It’s not surprising that a scientist (and the son of scientist) would go for that.  It is surprising that more partnerships don’t.

Also, we both like wine.  

4. 

How does you law degree help you in your life as an entrepreneur and author? Any tips & tricks as you navigate throughout your day?

In a simple, practical way, as a lawyer I can handle many of my own contracts, certainly for smaller projects, and can be an additional set of eyes on bigger contracts.

The more abstract and, imho, more powerful way my legal training helps is in understanding how to make an argument. The practice of law is structured around making an argument, or advocating for something. Taking a situation, breaking it down into its component parts, then repurposing those and retelling the story in order to achieve a goal. Any worthwhile presentation, speech, performance, movie, book, blog post, slogan, piece of art, or any kind of communication—the best ones have a point of view. They’re saying something.

Understanding how the art of argument has evolved from Socrates and Plato to Thurgood Marshall and John JRoberts helps me create the arguments of art.

5. 

Working a day job can be intense: constant interaction with clients and coworkers, long hours and commutes, the pressure of deadlines. How can we use humor to create levity in the moments we need it most? (Can you provide examples?)

First, if you’re wondering if a joke is appropriate, it’s not.  Especially in a professional setting. When in doubt, don’t. Just don’t.  

Second, don’t try to be funny. Just be yourself. Make light of your own insecurities or concerns or failings—that’s honest, that’s human, that’s self-deprecating. That’s the safest and most genuine form of humor, especially for the workplace. Make yourself the target.

Third, related, don’t make anyone else the target of your jokes, whether they’re coworkers or groups of people outside the office (though you can always make fun of the NY Yankees).  Don’t make assumptions about your colleagues, their beliefs, or their communities. Self. Dep. Re. Cate. 

Fourth, an exception: You can make fun of a “common enemy.”  If you’ve got a hard-a** client or superior or a crappy commute or the weather is a mess—and you’re sure everyone feels the same way and neither your boss, the client nor the meteorologist are around—acknowledging that common stress and pressure is a great way to relieve it. To let everyone know, “Yeah, we all feel the same way.”  Poke that bubble with the pinprick of humor.  

 “...if you’re wondering if a joke is appropriate, it’s not.”

A few final quickies:

Favorite podcast (other than your own:): I don’t listen to podcasts. I make ‘em, but don't listen to ‘em. Does that make me a bad person? Probably.

Favorite comedian ever:  Kurt Vonnegut

Best thing about being a Dad: The audience is easy to make laugh. So far.

Favorite way to unwind after a long day: Unwind? What’s that? Cooking. I like to cook, gets my mind outta my head.

Most recent $ splurge: New fridge

Most recent $ save: Old computer (8 years!)