How to Be Authentic While Making Difficult Decisions (Self-Awareness)

Photo: Pixabay/Geralt

Chapter 3 From The Power of Authentic Leadership

What I find really difficult is making career decisions. Normally it will take me two weeks, until the very last minute and I have to say yes or no. For a couple of weeks, I will tune everyone out who is giving me advice, so that I can make a clear decision on my own and it takes time.” — Paul Walker

Jared Kleinert is a superstar award-winning author of 2 Billion Under 20, TED speaker, successful entrepreneur, and an overall awesome guy. I first met him after seeing him speak at the National Speakers Association Conference in Washington, DC, in July of 2015. We connected at the event and ate lunch together after he spoke. He also introduced me to several other successful speakers who became friends and valuable connections of mine. I resonated with Jared’s energy. In November of 2016, we reconnected and had the pleasure of spending the day together in New York City.

What I love about Jared is that as successful as he is, he’s down-to-earth and genuine. He didn’t have the vibe or aura of “I’m better than you” even though his level of success is incredible. When we first met, I remember a number of people coming up to him and talking to him. He could have dismissed me as a nobody or told me he didn’t have time to speak with me, but he invited me to lunch. On top of that, as I said above, he facilitated my introduction to some big names in the speaking industry. Awesome, right? I say this respectfully, but I’ve met a lot of people in my day — some who are part of the National Speakers Association — who didn’t have the common decency to treat me like an equal. Jared definitely wasn’t one of them.

I’ve made it a point to only feature genuine and authentic people in this book. Here’s the first big lesson I learned from Jared, and it came from him leading by example: No matter how successful you become, stay humble and treat others with respect. Too many people let success go to their head, in the sense that they then think they’re above others. By all means, be confident, fully believe in yourself, think big, and act bigger. At the same time, please don’t become so full of yourself that you forget to be decent to others. This is crucial to your ongoing success. I’ve met people who got big heads because of their success and started to treat other people like garbage — which ironically limited them achieving more success. (For more on what I’m referring to here, check out the second chapter of my book Reach Your Mountaintop.)

I had the honor of speaking with Jared on the phone to pick his mind about his success for this book. We also hung out in New York City for a day during the weekend and helped one another with the projects we have going on. Be sure to check out his book 3 Billion Under 30.

Photo: Jeff Davis

Core Realizations on His Way to Success

“I’ve been an entrepreneur since I was 15- going on 16-years-old,” Jared said. “I worked for companies in Silicon Valley doing unpaid internships.”

Right off the bat, we see that Jared surrounds himself with world-class talent and people of high-level success. By taking the initiative, being proactive, and making a powerful internship opportunity happen at a young age, he exposed himself to opportunities that wouldn’t have been there otherwise. This has been a powerful factor in his success.

“What really opened me up to a whole new world of connections was when I attended the Thiel Foundation conference and met influencers from around the world. When I left that conference, I started to really inspire others. I also encouraged others to join in the craziness of entrepreneurship.”

“That’s awesome,” I said to Jared. “Surrounding myself with the right people was a huge turning point for me, so I’m definitely relating to you here. As this process was occurring and you became a man who inspired people all around the world, what are some of the key insights you had? Take me into your core realizations.”

“I realized that my insights helped not only young people but also people in the corporate world and older generations as well,” Jared said. “My book 2 Billion Under 20 has helped people of all different ages. I also realized it’s important to understand where your life is coming from. What I mean by that is being aware of and understanding the biases people have. Take into consideration those biases when figuring out what you want to do. For example, once you are aware of the biases it will help you to choose options that give you more optionality in life, instead of diving into something you don’t know for sure is what you want.”

What Jared is saying here is that when you become aware of the biases people have based on their background and experience, it increases your options. Think of it like this: It’s like being in a ballgame, and instead of going crazy trying to beat the other team, it’s about increasing your awareness enough to realize that there are entire new stadiums and ballgames to enter into. Another great analogy is that of a landmine. There’s nothing worse or scarier than walking through a mine field when you don’t know where the landmines are. But when you know where they are, you can actively avoid them. That’s what Jared is talking about. Being aware of what you don’t want allows you to avoid potential missteps and more effectively get to your desired destination. It also allows you to take people’s prejudices with a grain of salt, respectfully reminding yourself that their background may not apply to your life situation and goals.

“For example, if you are not sure whether or not you want to go to college,” Jared said, “take a gap year instead of diving into something that may not be right for you. I like to emphasize the importance of increasing optionality. You can live anywhere in the world. As James Altucher says, live your life, not someone else’s. It all comes down to how you make decisions. Are you going to listen to people who don’t really know what they’re talking about when it comes to the industry you want to join? Don’t do that.”

“That makes complete sense,” I said to Jared. “You’re a successful guy and very well-connected. How have you become authentic and what do you do to maintain such a large network?”

“Part of being authentic is having authentic interactions with people,” Jared said. “Openly share your obstacles with others. As you build your network, it can be hard to manage all those connections. To balance that out, make sure you have meaningful and authentic relationships, interactions, and conversations. I also make sure to only bring certain people into my network. This may be perceived as inauthentic by some people, but there’s a big difference between being a jerk versus being selective. You can be authentic while choosing to not connect further with certain people because they’re not the right person for you.

“Treat people with respect, but choose to spend a lot of your time with people who lift you up. These are two different things.”

I love what Jared is saying here, and I resonate with it. I always do my best to be respectful to others, even when they’ve given me reason not to be. On a rare occasion I might express some frustration if someone has really crossed the line and done something inappropriate, but as often as I reasonably can, I am kind because you never know what someone else is going through. Here’s the thing: a lot of people get this confused and mixed up. They think that if you’re kind to someone, it means you have to include them in everything you do. This is not the case. Make someone feel good about themselves and maintain cordial relations, but don’t have a false sense of obligation that you have to include someone in your daily operations if they aren’t a good fit for you. This took me a long time to learn, and I wish I would have learned it earlier on in my life.

“How do you maintain being humble while you are achieving at a high level?” I asked.

“I make sure to not treat people differently based on how they might fit into my relationship-building efforts,” Jared said. “Someone I meet may not be the best fit for my network, and they may not be someone I desire to stay connected to over time, but I’m going to make certain I treat them as an equal and with respect. The last thing you want to be thought of is a jerk or someone who treats people badly.”

“That’s so beautifully said,” I said. “A lot of people never learn or understand this lesson, and it limits their success. They think it’s okay to treat people like garbage, but in doing so, they end up sabotaging themselves. It’s definitely okay to be assertive and stand up for yourself when and where necessary, but someone shouldn’t be a jerk just because they can be. And more often than not, people are jerks for no reason other than they enjoy being jerks.”

“I agree,” Jared said. “Looping back to what you asked me earlier in terms of being authentic, I also want to point out my style of relationship building. What I do is find common ground, opening the playing field up to the other person and meeting them where their interest is. I’m fully conscious of making sure I spend time with the right people. But I don’t want to be a bad person, so I’m always respectful to others. This is a HUGE thing to remember when leading authentically.”

Jared just touched on part of his core genius, and what he said is so powerful it’s worth repeating: Open up the playing field to the other person and meet them where their interest is. Although Jared will not spend time with the wrong people, by showing genuine interest in others, he increases the likelihood that a genuine friendship and connection will occur.

We’ve now arrived at a crucial insight. Integrating this idea into your life will cause your prosperity to bloom:

Treat people as equals and be respectful to others, even if they aren’t the best fit for your network. The last thing you want is to be thought of as a jerk or someone who treats people poorly.

Remember, you can’t give away what you don’t have, and what goes around comes around. If you give people judgment and negativity, that’s what you’ll get back. If you judge others, that’s what you’ll get back. This is not a feel-good motivational saying; it’s a statement of fact. If you aren’t sending love to others, it means you aren’t a loving person. Let’s follow Jared’s example and implement his mature realization into our daily lives: How you treat others is an important part of your prosperity and success.

What is the Core to Leadership?

“Like everyone else I’ve been interviewing for this book, this is really valuable information,” I said to Jared. “I know there are a lot of people out there who look up to you, and you’re a leader. What are your thoughts on leadership and how it ties into achieving prosperity?”

“The more I can speak openly with people, the more people speak openly with me,” Jared said. “You have to be willing to take feedback from others. It’s not the easiest thing to hear, but the more objectively I can take feedback, the more objectively I can handle leadership. Getting feedback also helps me from a decision-making standpoint. It’s a balance between subjecting yourself to the input from others and being emotionally intelligent enough to know when not to listen.

“Get to know the people who work for you. For example, I sometimes have to have a difficult conversation with a team member, asking for feedback on a blog post or one of my other publications. The feedback may be shit, but if you hear that feedback, it’s very helpful.”

This ties in perfectly to what we’re going to hear from legendary blogger Jeff Goins in the next chapter, so stay tuned.

“Another thing on leadership I’d like to add,” Jared said, “is being able to see down the road a little bit. As I write and publish my books, as well as speak, I think about where that’s leading me and my business.”

Here’s the point: While leaders are busy focusing on the behavior necessary to take action today, they are simultaneously thinking about how what they’re doing today ties into where they’re going tomorrow. Leaders have vision. What vision do you have for your life?

How to Deal With the Craziness of Life

“What are some hacks you have to maintain your level of prosperity over time?” I asked. “What I love about your efforts is that you not only achieve a certain level, but you maintain it over time.”

“It’s important to really define WHY you do things,” Jared said. “That’ll keep you going over time. Also, understand yourself and how you make decisions. Anytime I feel like crap, or I feel down, I feel a lot better when I do some sort of gratitude expression. It might be looking at something uplifting on my phone or reminding myself of something I’m grateful for. I recently traveled from Cincinnati to New York, and I was absolutely exhausted from the trip. But I caught myself, and I took a moment to look up. I thought, Wow, I’m in New York. Taking everything in around me instead of getting caught up in my tiredness helped me to feel better. Also, smiling has a physical effect on your body. When you smile, it makes life less painful and more enjoyable.”

“Those are great tips,” I said. “I know you travel a lot. Is this for business, personal reasons, or both?”

“Both,” Jared said. “I left NYC for a few months because I wanted to not see people. This was not for a negative reason, I just wanted to give myself some space to be creative without having the daily distractions. I did the same thing this past December as well. I’m a pretty social person, so a recent hack for me has been to take myself out of physical locations when I’m trying to do a launch or get work done. It’s like when you are trying to lose weight, it’s best to take the temptation of certain foods out of the house altogether. The same goes for your productivity.

“I’ve set up a consulting firm, and I take on multiple clients. Even with a lot going on, I keep delivering high-quality content, products, and services to entrepreneurs and aspiring business leaders of our generation. The vision — the goal — is to get our peers to act on their passions and solve society’s biggest challenges while doing it capitalistically.”

I love how Jared pointed out he makes money doing this. He’s one of the most genuine guys you’ll ever meet, and, at the same time, he also profits from doing what he loves. It’s not one or the other. Both are true: Some people think that authenticity and wealth are mutually exclusive, but as we’ll discuss more later in this chapter, this is not true.

“While I speak for higher and higher fees,” Jared said, “I’m also interested in exponential ideas and actions, and in trying to do much bigger things. This might mean doing an online course, or something similar.”

Things are going to be hectic on a daily basis. That’s life. But don’t forget the end game and where you’re going. Look for ways to exponentially increase your success.

Making Difficult Decisions Leads to Exponential Success

The purpose of this book is for you to activate the keys to being authentic so that you will achieve prosperity, which includes mental, emotional, spiritual, financial, and physical health. In order to maintain your authenticity during difficult and trying times, you must have a framework for making difficult decisions. This is important because poor decision-making leads to stress and unhappiness. Please know that many of your decisions may turn out to be wrong decisions in the fullness of time, but with these tips from Jared, you will know how to make the best choices given the information you have in the present moment.

As we continued with our phone discussion, Jared opened up and told me more about his journey.

“I never went to college,” Jared said. “Society would judge me as a bad decision-maker.”

Yet Jared is the epitome of true success because he has defined and gone after his own version of success. He’s started a successful company, Kleinert Ventures, where he consults with #1 New York Times bestselling authors, Fortune 500 companies, and VC-backed startups on product launches and overall marketing strategy. He’s coauthored and published a book that’s shelved all over the world and has sold thousands of copies. He now charges $10,000 as a keynote speaker to travel around the world and speak at conferences, colleges, and corporations.

“I have a network of friends, influencers, and mentors who deeply care about my success and well-being,” Jared said, “and I’ve created incredible optionality for my future to start new businesses, create wealth, and invest in interesting life experiences.”

Here’s the point, and this is all shared for your benefit and for your enlightenment:

“It’s because of the seemingly ‘difficult’ decisions I’ve made,” Jared said, “that I’m able to achieve exponential success and impact, as opposed to making ‘safer’ choices that would actually be detrimental to my future, but seem ‘by the book’ to others around me.”

Read that bold sentence above at least one more time, because it is without exaggeration one of the most powerful statements I’ve ever heard in my entire life. I WISH I WOULD HAVE HEARD THIS EARLIER (I get so passionate about this because no one ever shared with me these kinds of valuable insights when I needed them most, which motivates me to help as many other people as I can). But here’s the silver lining and best part of this process: It’s never too late to let go and start over, making the decision you’ve always wanted.

A Few Thoughts Before We Dive Further

As big and bold of an entrepreneur as Jared is, he does acknowledge and balance out doing work that matters with work that pays the bills. At the same time, there are ways to make money from doing what you love, and Jared is a great example of that.

“There are some cases where ‘success’ for you will require a more traditional path,” Jared said, “like becoming a lawyer, doctor, or dentist. That being said, there are ways to accelerate your career and life even if traditional decisions are necessary to make.

“Also, I assume you want to deviate from the norm. If you are okay with the status quo, then, by all means, stay where you are. However, if you are reading this, there’s a good chance you are growth-minded and want to continue developing new skills, advancing your career, and developing decision-making abilities.”

If you’ve read this far, you’re all-in. Let’s go further.

Aligning Mission and Money

“There are people out there who have a passion or serious activity they take part in,” I said to Jared, “but they don’t make money from it. Is it feasible for someone to get paid doing their calling?”

“Yes,” Jared said. “Let me use my publishing journey as an example. My mission is two-fold. I want to get as many people as possible to act on their passions in life, and then unite in solving the world’s most pressing problems.

“My first book, 2 Billion Under 20, had this mission, but because we went with a traditional publisher, all financial incentive to share the stories in my first book disappeared after the first few weeks of publication. The publishers owned the content, made money with each copy sold, and didn’t care about our mission like we did. Their job is to sell books across hundreds, if not thousands, of titles each year, and so their big ‘mission’ is to generate sales regardless of the author whose books sell the most.

“By ‘professionally self-publishing’ 3 Billion Under 30, I align our mission with money. I can apply industry-leading marketing strategy to the book’s launch and sales over time because I control all aspects of the process. Every time I sell a book, I make money, and therefore I’ll be indefinitely incentivized to share the stories of individuals who have invested their time and energy into helping me carry out my mission.

“For most people, however, this isn’t the first decision that is considered, even though you could make the argument that it is the most important. In fact, traditional publishers are usually considered due to an author’s lack of ‘product’ knowledge (how to make the book), ego (dreaming of hitting a credible bestsellers list), or because it is simply the standard path. All of these are bad ways to make important decisions.

“Here’s a better way. Ask yourself, What are my goals business-wise? Mission-wise? It is possible to align purpose and profit once you are clear on your answers to the questions mentioned above. Elon Musk runs SpaceX to make humans multi-planetary as a way to avoid existential crises, and also to make money. TOMS Shoes helps those in need while also operating as a for-profit company.

“In both cases, and almost all others, where the purpose-profit alignment is clear, the companies actually make more money, have a better culture, and mean far more to their customers than if they solely operated to drive a mission or to make money.

“Simply put, I see this new publishing model as the best way to make this change in my business, and I have an obligation to myself and all those who have contributed to the 3 Billion Under 30 mission to put financial incentive behind our work as much as possible.”

Let’s stop and look at an important reflection point here because this point is subtle yet incredibly powerful: To authentically align mission and money, you must improve your decision-making ability. You must step away from the “normal” and “expected” decisions; instead think creatively and outside-the-box like Jared and other luminaries. Following a traditional decision-making process often leads to losses and failed ventures.

Incredibly enough, my publishing journey is remarkably similar to Jared’s. I went through a traditional publisher for my first book and while it was a valuable experience and I don’t regret doing it, the publisher kept all the profits from the print sales of the book. With my second book, I got a little smarter. I self-published and kept more of the profits from book sales. For the record, making money was NOT the main purpose of publishing the book. The main purpose of Reach Your Mountaintop was to spread an important message about how to get through dark and challenging times, find the silver lining in your life, and live your own version of success. With that said, here’s what Jared and I are telling you: There is a way to authentically make money while helping others, living your purpose, and doing what you love.

For the longest time, I believed people making money to be inauthentic. This was a misperception on my part. Focus on how you are making money and why you are making money, seek non-traditional paths and options, and you’ll find that there are more ways to make money with your business than you may have initially thought.

With decision-making being such a crucial part of authenticity, you must be asking right now, “Jeff and Jared — this is all great and makes sense. So HOW to do I make decisions?”

I’m glad you asked.

How to Make Difficult Decisions

“Whether or not you’re an author or entrepreneur, hopefully our discussion up until this point will have opened your eyes to the level of thought needed to provide your own friends, customers, and individuals in your life with value, care, and engagement,” Jared said.

The following is a checklist to follow as you make difficult decisions.

See Who Else Has Made Similar Decisions

“When I decided not to go to college, it was in part because many reputable thought leaders spoke out against its validity,” Jared said. “The Thiel Fellowship, UnCollege, Enstitute, and other programs showed there was an alternative for some of our generation’s outliers.

“I looked for alternate paths by seeking council from those who had made similar choices and succeeded, not opinions from those who’d never considered a different path and therefore had tradition (and their choice to abide by it) to protect.

“In my career, my family and mentors showed me that entrepreneurship would be the right path for me, especially creating a ‘solopreneur’ type consulting path. This path would allow me to work with high-level individuals and pay the bills in only 20% of my working time while investing the remaining 80% of my hours into longer-term projects like 2 Billion Under 20 and 3 Billion Under 30. These long-term projects would take years to network, build, and ultimately develop into a sustainable and scalable business.

“Between reading The 4-Hour Workweek, attending some events from marketing legend Eben Pagan, and working for a VC-backed startup since sixteen, I soon realized that no one cares about your degree so long as you get the job done. There are ways to build networks, skills, and companies that don’t require traditional paths or prerequisites.

“All of this I learned from studying the successes and mistakes of others before jumping into similar difficult-seeming decisions myself.”

Seek Subject Matter Expertise

“In addition to studying those who made similar decisions, other information can be sought out to protect the downside of difficult decisions should you continue your pursuit of them upon further review,” Jared said. “For me, this additional knowledge almost always comes in the form of mentorship or consulting with people who have deep knowledge on very specific questions or factors I’m still considering.

“You can see this in the consciousness of our marketing plan for the book launch. Not only did I study those who have made similar ‘professional self-publishing’ moves in the past like Tucker Max, James Altucher, Kamal Ravikant, Taylor Pearson, and others, but I also then sought out the specific experts for email marketing, or paid advertising, or design.

“With each new conversation comes the opportunity to solidify your stance on a pending decision, or change it because you are unsure that the bet you’re making is worthwhile.”

Lose Your Ego and Make Your Decision Scientifically

“Even after gaining all this knowledge on the industry and being in a position to reasonably bet on which decisions are best for you, our egos get in the way of us executing those difficult decisions,” Jared said.

“For me, it means giving up the possibility of making a New York Times, Wall Street Journal, or USA Today best sellers list for at least the first half of 2017, if not forever, in order to pursue meaningful sales and collect customer data. Only sales registered through retailers and Amazon count for those lists, all of which have complicated algorithms for selecting who gets featured. And, while I’d love to be on those lists personally, it is more important for 3 Billion Under 30 to speak to as many potential readers as possible and be in a position to provide those people with as much value in the future as possible.

“Also, in order to finance the team I hired and the first print run for the book, I needed to raise a small amount of money from family and friends. My ego hated this idea because I’ve never asked for help financially in my adult life. From a numbers perspective, it was an intelligent business decision, because I only need to hit five percent of our sales goal for the book in order to pay everyone back.”

Build Yourself a “Safety Net” by Increasing Optionality

“The good thing about making difficult decisions is that almost none of them are irreversible or everlasting,” Jared said. “If you’re stuck on what to decide regarding your education, career, or other situation involving a seemingly difficult decision (like whether or not to go with a traditional publisher as an author), always default to decisions that increase your optionality.

“By creating something like 3 Billion Under 30, I’m building hundreds of deep relationships with influential individuals who would hire me in a heartbeat or otherwise refer me to new opportunities should I ever have issues with money or need a job.

“Instead of skipping school outright, I took two gap years. These were time periods where I tested other decisions but could have reverted back to being a student at any point in time.

“By becoming a solopreneur or consultant rather than being an employee to one company, you allow yourself the option to work with multiple companies and earn multiple contracts or income streams rather than relying on one organization to cut your paycheck.

“Launching a book in a way that doesn’t rely on sales in a specific window of time, and financially incentivizes its author to sell copies indefinitely, provides optionality for how and when to sell product.”

Straight to the Top

In order to land an opportunity speaking to the entire National Speakers Association in Washington, D.C. — the conference where we first met — Jared connected directly with the President of the NSA. He went straight to the top, and effectively connected with someone of power and influence. This strategy is a part of his core genius. You can bang your head against the wall for years on end trying to get through assistants whose job it is to block you. This insight alone could, without exaggeration, change your life (as it certainly changed mine).

I get that the head of a given organization may not have their email address or phone number available to the public, but if you do some digging, it may be easier to find than you initially thought. You can also ask someone you know and trust to refer you to the head of an organization, or someone near the top. Many people assume that the President or CEO of a company or organization is untouchable and out of reach, and that becomes their reality. But more often than not, these influential people are in fact reachable. Remember, they are people just like you and me.

One quick caveat and reminder: Don’t let other people limit you. I was recently inside a company’s building for an event. I was not there to specifically meet with the CEO, but I happened to notice he was available in his office. I walked in, introduced myself, and had a great conversation with him. This interaction led to some awesome things. After I left the office, despite it being a positive interaction, I received negative feedback from two employees of the company who felt I overstepped my bounds and was out of line to walk into the CEO’s office.

Their negative reaction was more a reflection of their own biases, self-imposed rules, and limited viewpoints than it was the truth. Who cares what they think? I had the guts to authentically say hello to an influential business owner, and it led to wonderful things. Just because someone doesn’t approve of your actions doesn’t mean you are in the wrong.

“How are you able to reach so many people?” I asked Jared.

“I may only specifically connect with fifty to seventy-five people,” Jared said. “But I’m strategic about my efforts. Those fifty or seventy-five people, through their followings and businesses, each influence millions of people. By influencing a small number of successful people, my efforts end up reaching millions of people.”

This is the secret embedded within Jared’s strategic thinking. It makes perfect sense. Think about it. If you go into a given company and want to make a difference in that company, you are much better off speaking with the CEO than with the employees. The CEO is the one who can endorse you, invest you, hire you, etc. (whatever your business goal is). This is absolutely nothing against the employees of the company, as those would make for good conversations as well, but what we’re taking into account here is your business goal and the strategy necessary to most effectively achieve it. Why talk to the gatekeeper when you can go straight to the person who has the key to the castle?

Make a Decision

“Take these tips and turn them into an action plan of your own for authentically deciding upon a difficult decision in your life and executing that choice,” Jared said. “The opposite of increasing optionality is crippling yourself through indecision. Every day you don’t act, the opportunity to make a difficult decision wisely and effectively becomes more challenging and less rewarding.”

Let’s model after Jared and be strategic about our decisions. By following the process laid out here and stepping outside the norm, we will find ourselves achieving exponential success and fulfilling our true leadership potential. We will make an awesome difference in the world.

Jared Kleinert is a TED speaker, award-winning author, and success expert. He was featured in Chapter 3 of The Power of Authentic Leadership: Activating the 13 Keys to Achieving Prosperity Through Authenticity. This book features a billionaire, two Senators, New York Times bestselling authors, icons, and world-renowned leaders. These experts offer you a deep dive into mastering the power of authentic leadership, achieving prosperity, and helping others the way you were meant to help others. This book is free on Kindle through the end of Friday, June 23rd, 2017.

Jeff Davis
Jeff Davis is a professional speaker and the author of several books. He has done keynote speeches internationally and is a sought-after expert on self-leadership, anti-bullying, and overcoming adversity. Jeff frequently speaks to high schools, colleges, nonprofits, organizations, associations, conferences, and businesses. He’s been to five different continents and has a Master’s degree from Johns Hopkins Carey Business School. He also did a well-received TEDx talk in New York City.