The Art of Audacity

In the first half of the 19th Century Carl Von Clausewitz, a famous German General and tactician wrote that “Given the same amount of intelligence, timidity will do one thousand times more damage in war than audacity.”
While attempting not to sound overly dramatic, I would argue a similar case for both the workplace and life. Audacity, in the long run, will outperform timidity in making your life fulfilling. Without the occasional dose of audacity, you become easy to ignore, and even worse, easy to predict. The advantage does not lie in being temperamental, but in the lingering thought in your boss’ mind that you just might do X.  They won’t make assumptions on what salary you will settle for or timeframe is acceptable for promotion, or that you will simply stay with the company because you are too timid to take a risk.

It took me eight years in the corporate world to learn this lesson. I spent my twenties following along with what my bosses asked me to do, moved where my bosses asked me to move, and generally followed the path of what a successful 21st century business person should do. I bought a new car! And a house! And then another house!
But I’d taken no risks. I had little I could point to that I was proud of. I’d never stopped to write as I’d always wanted to. I’d never had the guts to say “no” to a boss when asked to complete a project or move to a new city. But it wasn’t because I wanted to. It’s because I thought I was supposed to. I was still working along a path that was safe. But I had been timid. I found myself in the same place that AJ Leon found himself in at a Wall Street Bank in his mid twenties. When his boss offered him a promotion, he looked into the future and saw that without the audacity to do what he wanted to, to do what made him want to get out of bed on a daily basis, he would end up exactly where his boss was: Rich, in a business he cared little for, and most importantly miserable. Most people’s audacity will not reach to the level of AJ’s. Yours may be a hard negotiation. A step into a part of the business you’ve been told not to take, but that calls to you. Or an entire career change altogether.
In life, work, sports, sales, etc. with everything else being equal, audacity and aggression will win more often than timidity. Is that fair? Of course not. But what is? Get the thought of “fair” out of your head. Take a good hard look and ask yourself, if you were to do something audacious in your life, or in your work right now, what would it be? Now, don’t go do it just because, but think hard about it. Is it something that you truly want to do? If so, chances are you should.


The Mindless Bureaucrat of Your Own Paperwork

Some may refer to it as procrastination, but being the mindless bureaucrat of your own paperwork is a much more dangerous version of avoiding quality work. What does the phrase mean exactly? Consider this example:
You have a project in mind that you have started or would like to start. But before you can begin, you need to do “X” amount of research. And don’t forget that your outline isn’t finished yet anyway. The market analysis isn’t going to do itself either. You need to get 360 degree feedback. And you can’t very well do this correctly without a SWOT analysis, can you? And let’s be honest, your business plan could use some rounding out. I guess you’ll just have to keep chipping away at the edges before you can really dive in!
Working on these things are all beneficial, and over time are certainly things that you need to do. And yes there are certainly benefits to getting as much of it done as you can before fully committing. But there is also a point at which you are creating a bureaucracy of your own, and are only limiting your efficiency. You are settling for the dopamine hit of crossing an item off your list rather than creating real substance.
We all know what these activities look like in the workplace, particularly in a corporate setting. But often, we create them for ourselves as well. We become focused on working on a process instead of working on a product. And that’s the sticking point. Make sure you are making progress on your product, whether that is an app, a blog, a book, or whatever your day to day gig is asking you to deliver. No matter what you do for a paycheck on Fridays or as a side hustle when you have time, never forget to stop occasionally and evaluate the impact of the work you are doing. The perfect circumstances to “get started” or “go all in” will never arrive. They will never magically align and you will never be able to push or pull them into place either. Make strides everyday.

Figure Out Your Own Scorecard

The important question to consider here is whether or not this is a kick in the pants you need (possibly,) or more likely, are you getting caught up in the heat of the moment and judging yourself on someone else’s scorecard?

Most of us know the feeling, when you get together with old friends, colleagues, or schoolmates and rears its ugly head. It might be at a party, dinner, or even college reunion, and suddenly you are listening to what other people are doing with their lives, or their careers, and something inside you immediately compares yourself to them. Just days before, if asked, you would have expressed little interest in private equity, oil and gas, software development, or an app-based startup. You would have ranked work life balance as one of your more important goals, but after talking to Zach who is in investment banking and hearing about his recent trip the Swiss Alps, you are now thinking about your next promotion and how you need to work harder to get there. You find yourself talking to others about the great potential opportunities ahead of you, possibly exaggerated. And justifiably so. Who wants to be left behind?
The important question to consider here is whether or not this is a kick in the pants you need (possibly,) or more likely, are you getting caught up in the heat of the moment and judging yourself on someone else’s scorecard?
During just such one of these get-togethers recently, full of go-getters all in their late twenties and early thirties, I first encountered the idea of “figuring out your own scorecard.” In reference to a friend who was constantly posturing on his expensive purchases and work life, none of which seemed to fulfill him in less than superficial ways, another friend quite simply and accurately said, “Yeah, I think he just needs to figure out his own scorecard.”
What a wonderful way to phrase it. Have you defined what you are working towards in your life, whether it is a degree of happiness, achievement, or creation? Is it really that new car you drive to the reunion in order to leave a good impression? Is it that Instagram worthy vacation you only get to take once a year while you break your back for the other fifty one weeks? Is it the promotion that you don’t really want because you don’t like your work, but will look impressive on your LinkedIn? Take some time to really develop and hone your scorecard both inside and outside of work. Are you making strides in a passion you have always dreamed about? Learning a new language? Learning a musical instrument? Working on your relationship with your significant other? Working towards the ability to live abroad? Or work from home?
The easy thing to do would be to play with the scorecard society gives you, and think simply of promotions, cars, vacations, and things. While none of these things are bad in and of themselves, they can be dangerous when you use them to supplant those things that you truly want. That scorecard chock full of these items leads down a path that unfortunately does not include happiness or fulfillment. So instead, work backwards. What would be fulfilling to you? What would actually make you happy? Now what do you need to get there? Start doing something every day, no matter how small, that makes progress on that path, or makes a tally on that scorecard.
Oh and trust me, those things, those passions you are pursuing, make you much more interesting at parties anyway.

How to Filter Constructive Criticism

Annual Reviews. Six month reviews. Weekly check ins. Three hundred and sixty degree feedback. Emails. Instant messengers. The modern workplace is an environment of constant feedback (whether you want it or not). I won’t even get into the dangerous feedback loop that is social media. But with current technology and the speed of communication, criticism and feedback is offered to the modern employee, artist, writer, athlete, etc. in a constant stream that can sometimes be debilitating.
However, contrary to some beliefs, not all criticism is useful. But our society has swung the pendulum to far side of acceptance when it comes to listening to other’s thoughts of our work. Do we need to keep an open mind and listen to criticism? Absolutely. But does that mean that everyone’s opinion of what we are doing is important or insightful? Absolutely not.
So how do we learn to let go of criticism that we have listened to and considered but know needs to be discarded? How do we keep it from bouncing around inside of our heads and stopping us from instead focusing on the work that we need to do? The two people who I believe who have phrased it best in fact have lived thousands of years apart.

Buddha: If someone gives you a gift and you choose not to receive it, to whom then does the gift belong?

Bozoma Saint John: Sometimes critics are just people who can’t see the world the way you see it.

Both of these quotes very simply highlight the fact that criticism in and of itself is not valuable. Obviously there is the danger of blinding yourself to criticism that is useful, simply because hearing it is painful, but as the Buddha says, it does not belong to you simply because someone offered it. You can reject it.
On the other hand, as Bozoma says, someone else’s understanding of your work can be as fundamentally flawed as a basic view of the world. This often happens to pioneers in various fields who are challenging foundational rules previously thought to be unbreakable. The critic’s opinions are not valid because the critic is not yet capable of understanding even the basic premise on which the work is built.
As you go about your daily life, building in these two filters will become integral to your mental health and the quality of your work.



If you have not taken the time to read Bronnie Ware’s book Top Five Regrets of the Dying, or at least her essay by the same name, take some time to do so. As a palliative care nurse, Bronnie spent more of her life listening first hand to the final regrets of terminal patients than most people could likely stomach. However, in her book, she relays the most important messages you could receive from these patients, no matter what stage of life you are currently in. Have you made the mistakes below already? Well, good news for you, you have time to fix them. Are you still to young to regret anything except how much you drank last Friday? Don’t make these mistakes. Beware the below:

1. I wish I’d had the courage to live a life true to myself, not the life other’s expected of me.
2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish I had let myself be happier.

At least one of these should resonate with you if you spend just thirty seconds considering them. If none of them do, then feel free to go back to your perfect life and leave the rest of us to commiserate. Number one and number two hit me like a ton of bricks. People who literally have nothing to lose and no reason to lie, expressed pain and regret regarding two things fundamental to American life and culture: fitting in and making money. If that doesn’t scare you, it should.
If you have ever worked in a corporate environment, then you have likely thought about at least one of these top five regrets. If you’ve turned down something that fascinates because it is not “stable” enough, or because it doesn’t make enough money, then you should be scowling down at #1. Almost everyone in America can catch feels for #2. Does that mean that if you are not “following your passions” for eight hours a day then all is lost? Of course not.
But take a look at these regrets and do some soul searching. Are you doing something everyday that you love? If you hate your 9 to 5, are you doing anything to make that job unnecessary? When you do something simply because you’re expected to, and it stabs you a little deeper each time, are you taking any steps to shed that mask? We all go through life thinking how far away death is, or how much time to have to eventually chase what we want to do, or live the life we want to live, or travel to that country we want to see. But as Bronnie Ware found out, most people carry those desires around with them their entire lives and eventually run out of that most precious resource – time.

“Busy is a decision.”

Debbie Millman, the host of the podcast Design Matters, is also an educator, writer, artist, curator, and designer. In a recent book by Tim Ferriss, Debbie drops a piece of wisdom that hit me with a rare force. Everyone likely recognizes the feeling of hearing something that strikes them as absolute truth, and Millman’s words definitely created this feeling in me.
In response to the question, “If you could have a gigantic billboard anywhere with anything on it, what would it say and why?” Debbie replied simply, “Busy is a decision.” Let that one sink in for a minute and consider what she means. There is no more perfect and concise way to put it.
When it comes to to getting things done, or more importantly not getting them done, Debbie rightly says that there is no more inauthentic excuse. Think about something you wish you had done over the past week, month, or year. Why didn’t it get done? If your brain goes straight away to “I was just too busy” or “I had too much to do” or any variation of that thought, you are not fooling anyone but yourself. What you are really saying is that whatever you wanted to accomplish simply was not important enough. It was not a priority. You clearly did a lot over the past week, month, or year, but this project, goal, or aspiration was not as important as you claim it to have been or you would have done it.
To take this to the extreme, why did you not stay at home last Wednesday to work on a side project, novel you are writing, business you are developing, etc. instead of going in to work? The answer is likely because you need your job and the income that comes with it. Okay, fair enough. So your job took priority. Can you say the same about the TV shows you watched? About the Instagram feed you constantly checked? About the chores you did around the house? The shopping trip for clothes you do or don’t need? If you think back over your activities from the past set time period, and they do not in hindsight appear as important as what you would have liked to have done, then you have some serious adjusting to do. Saying you were too busy is just lazy. There are people who have gotten done what you wanted to do, but with less time than you had. The difference is that for them it was a priority.
Remember Debbie Millman’s words, “Busy is a decision.” Whether at work or at home, the next time you don’t get something done and are faced with the disappointment of it, try changing the narrative from “I was busy,” to “It wasn’t important enough.” You’ll find that it hurts a little bit more, and hopefully gets you moving in the right direction next time.

4 Steps To Taking Action

Mark Twain has numerous comedic quotes, many of which will get you a laugh (one of my favorites being, “Golf is a good walk spoiled”). Despite the cleverness, and seeming shallowness, of many of the quotes, however, the majority of them have a great depth if you are willing to stop and consider their realities.
One that is particularly applicable, both in terms of general life and business.

“I am an old man and have had a great many troubles, most of them never happened.”

How often in life do we let potential troubles, worries, or complications paralyze us? Take a good hard look at every aspect of your life including work, relationships, health, education, etc. Which parts are you truly happy with and which are you not? Which troubles, that have not happened and may never happen, are stopping you from improving the parts of your life that need attention?
What project would you like to take on that you are avoiding? What challenge is scaring you away? What major life change are you putting off? Humans are creatures of planning and forward thinking, which makes us unique. But when that forward thinking causes anxiety and keeps you from ever coloring outside the lines, then it’s time to get off your ass and shake things up.
Tim Ferriss has a wonderful chapter in The 4 Hour Work Week that encourages readers to do one simple activity:
1. Think of that change you have been wanting to make.
2. Imagine the worst case scenario if you take the leap and it doesn’t go well.
3. Then, realistically consider what steps you could take to get back to your current state (or close to it) if it doesn’t work out.
4. Now, think about what your missing out on by NOT taking the action (fulfillment, happiness, etc.)

Most likely what you are missing out on by not taking the action is scarier than the tangible objects, property, or money that you MIGHT miss out on if you take it. And even if you take it, and it doesn’t go well, you can likely recover pretty quickly! So don’t let the troubles in your life (that haven’t happened) stop you from pursuing what you should.

Sting Like A Bee

What I’m Reading:

Charlie “Tremendous” Jones has been attributed with one of my favorite quotes:

“You will be the same person in five years as you are today except for two things, the people you meet and the books you read.”

These days I think you can also add blogs and podcasts underneath books, but the principle is the same. When you finish your normal 9-5 (do jobs with these hours still exist?!?!?), do you go home and turn on the TV and space out to The Bachelor, or The Voice, or whatever new show is based in Chicago? On your way to work, do you listen to sports radio or play games on your phone while riding public transportation? There is nothing inherently wrong with these things, but if they are not directly tied to the industry that you work in, then you could be wasting valuable time.

Did you know there are podcasts that help you learn new languages that are just 15 minutes per episode? Did you know there are blogs that can help you create passive income in order for you escape the corporate grind and become an entrepreneur? Did you know there are books out there about…everything.

Make the best use of your time each day to read or listen to something that will make you a different, better, or more educated person in five years. I’ll share what I’m reading and listening to myself. Jump on the bandwagon with what I’m reading or use it as a springboard to find your own passions.

Currently Reading: Ali: A Life by Jonathan EIG

Muhammad Ali had a fascinating life. He knew from a very young age that he would “shake up the world,” and pursued that end with a dedication few others have matched. He was embroiled in the revolution of African Americans in sports, the Civil Rights movement, and the Vietnam War protests all while rising to top of his sport at the young age of twenty-two. He lived a life from which we can all derive inspiration, whether you loved or hated him. If you want to see what dedication to be the best at something looks like, check out this monster book. If the 500+ pages intimidates you, just do your own research on Ali. As long as you make sure it is from a reputable source, you will be in for a treat.

Become the Go-To-Guy (or Gal)

As I mentor younger employees or new employees within my company, they often ask, “What do I need to do to get promoted?”

Without diving into the numerous issues with that question, I usually begin in one simple place. I don’t go into the “Why do you want to be promoted?” or “What’s your motivation?” or “Are you running to another job, or away from this one?” Those could all be topics of different blog posts.

Instead, I explain to them that people who usually get the jobs they want are already doing them before they are paid for them. Often this only gets me a furrowed brow and a “What do you mean, Mr. Shamelessly?”

What I mean is that the person who is going to get that promotion will already have learned the ins and outs of it and begun literally DOING it before the opening is even announced. The person is not paid for doing these things, usually because they were not asked to do them!

I can already hear the chorus of readers bemoaning the above: they shouldn’t have to do work they aren’t compensated for. Or the ever-present, “Well, that’s not my job”. Well, tough shit, I guess. All is not fair. In fact, almost nothing is fair. You are competing against other people for this job that you want. Why would you not take the advantage if it’s there? What you’ll also find, is that as you get accustomed to doing the more complicated or different position, you not only get better at your own, but it will take you less time. Your time management skills either get better, or – more likely –  you have come to understand Parkinson’s Law (more on that another time…..)

Want some examples of what I mean? The Sales Manager at my company has to collect weekly sales numbers every Friday. He has to track down his sales people and account executives and collect these numbers, put them in a spreadsheet, and send them up to his boss. One of his young and upcoming sales people is interested in being promoted sometime in the near future. He asked me how he could get recognized as a go to person and distinguish himself when the time came. He wanted to know if his numbers would be good enough.

“Numbers only get you into the conversation. They don’t get you the job. You know how your sales numbers get collected by Mr. Sales Manager every week? You think he likes having to do that? Do you think your value would go up if, without being asked, you started collected those at lunch every Friday and sent it to him, so that he didn’t have to worry about it? Do you think the next time a bigger, more important project comes along, he will come to you or to someone else to help get it done? Whose name will end up on that project alongside his?” It took my mentee a moment, but once he understood, it all clicked into place.

That is a very, very small example that takes very, very little effort. However, that’s the point. It can have a large impact on the mindset of the person who will be promoting you one day. Start doing the jobs you aren’t paid for. You will become the Go To Gal or Go To Guy in no time.

Why Losing Is Better Than Failing…and the Difference

A theme that has been written about over and over again is the idea that you need to seek out failure and attempt things that make you uncomfortable. Working on challenges outside of your comfort zone not only teach you new things, but make you better at the simple act of learning, which is infinitely more important. However, this is a simplified idea that ignores the mechanics of what specific challenges learners will encounter. Josh Waitzkin, a fascinating student of the science of learning and performance has written a book titled The Art of Learning that addresses exactly this topic.

If you are not familiar with Josh, he was a chess prodigy who was the subject of a book and movie titled Searching for Bobby Fischer. I would highly recommend that movie for any who have not seen it. In The Art of Learning, Josh Waitzkin writes about his own learning process that helped him to win eight National Championships in chess and twenty one National Championships and several World Championships in martial arts. Anyone who can become world class at two such very different disciplines is someone worth listening to.

In one of the chapters, he writes about an incredibly powerful learning technique that I believe ties quite simply not just into business, but also the fields of Sales, Leadership, and personal development in general. Waitzkin calls it Investment in Loss. The core idea behind this principle is that while learning a new technique, we have to let go of ego. We have to be willing to lose. Most importantly let go of our tendency to push back (in the form of martial arts in which he competed, physically pushing back against an opponent’s push was a big mistake; the metaphor works for mentally fighting ideas as well). However, pushing back both physically or mentally stunted the growth and learning process. Very simply, Investment in Loss is the letting go of old habits.

How often are we confronted with something new and different and our immediate reaction is to stand our ground or even push back? How often do you see your coworkers, spouses, or children dothe same? How often are we willing to invest in a loss or two, face rejection from customers and prospects, in order to sharpen our skills and shorten our learning curve? As an energetic management consultant Carl Shoemer demonstrates in his incredible seminar on managing change, when a change is implemented, results immediately dip in the short term. However, this is how you assure your long term success. Those who understand this, fully embrace the downturn, a phenomenon similar to what Josh has termed Investment in Loss. When they reach the point of return on investment, if dwarfs the results of those who have not made any investment at all.

*This post contains affiliate links. But the book is still amazing. Give it a read if you want more info.