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5 Principles That Increase the Odds of Massive Career Success

Scott Trench
16 min read
5 Principles That Increase the Odds of Massive Career Success

If you want to move aggressively toward financial freedom, then there can be no debate that you must accelerate your wealth generation in some combination of the following four areas:

  • Spend less money
  • Earn more money
  • Generate greater returns on your accumulated assets (invest effectively)
  • Create assets and income streams

I typically write with a particular mind toward helping those in the middle- to upper-middle-class income range (and with less than $100,000 in investable liquidity) move aggressively toward financial freedom. And for that group, I believe that the most immediate impact is typically found when folks drastically cut back on their lifestyle expenses and develop a sound investment philosophy.

Related: The Simple But Profound Secret to Long-Term Investing Success

I believe that once you save a large portion of your median- to upper-middle-class income and invest it appropriately, it’s worthwhile to continuously experiment with side hustles and other entrepreneurial pursuits with free time in the attempt to accelerate progress.

And of course, I believe that for the truly aggressive, career paths with performance-based pay offer the potential to drastically accelerate earned income. Sales, self-employment, and full-time entrepreneurship give those pursuing these careers the opportunity to make far more than they might in a traditional career path. The risk, of course, is that these types of ventures often come with little to no base salary or benefits.

What I haven’t written about at length, but have invested an immense amount of personal time in, is in career development: Developing skill sets so as to advance rapidly within a company and access career opportunity.

Perhaps part of the reason that I have neglected this area to some extent lies with the fact that I have had such a relatively short career of my own: Who am I, with my five or six years of experience, to be giving career advice to folks who have many more years in the field?

Perhaps I’ve also felt that my career has been something that may be unrepeatable for many folks. I joined a company that has grown more than tenfold in the four years I’ve been here. I joined as the third full-time employee, and I find myself currently operating the business as president.

Perhaps I have been wary of sharing my philosophy with regards to career advancement because I believe that many folks may have spent much of their education, their careers, and their lives optimizing wherever possible. I think that many who earn a full-time, median- to upper-middle class income currently work in such a position because they believe that the job offers the best possible combination of pay, benefits, and long-term opportunity.

Frankly, if you earn more than $75,000 per year or have a path toward getting to that number (or even $100,000 or more), then you are doing pretty well on the career front. You may find it difficult to drastically increase income generation from such an already strong position. And you may not need to drastically increase your income to speedily move toward financial freedom.

Lastly, I think that many people simply may not want to follow this career advice and the eventual path it leads down. The path that I’ve gone down has led me to want to be a leader and a manager. I love and work with enthusiasm on organizational challenges that many detest. I like both building hard technical skills and industry expertise and working on the soft general skills necessary for effective leadership and management.

Regardless of my past reasons for not diving into this, I am now writing this article, in which I share some concepts that I believe have been helpful to increasing the odds of success in my own career.Today I find myself president of BiggerPockets.com, and in the privileged position of leading our team of 23 full-time staff, dozens of wonderful volunteers, and over one million community members.

With that, here are what I believe to be the five keys to increasing the odds of a positive career trajectory.

1. Relentlessly Demand Competence

I seek to surround myself with people who are able to succeed in a variety of life’s challenges. I believe it is a risk to become so specialized that you feel that it is a step back in your career to learn a new skill or become an expert in a new area. Today’s workplace demands a different skill set – the ability to rapidly develop a high degree of competence in new skill sets on the fly, in a matter of days or weeks. This skill of rapidly developing competence in a wide range of business skills is something that I seek to develop personally, and it is also what I expect my colleagues and team members to embrace as well.

Instead of working toward total mastery in a single field, I work on the ability to develop expertise and operate professionally across a wide variety of disciplines, and surround myself with people who have the ability to excel in multiple areas as well. I also don’t choose the subject matter of my self-study randomly. I purposefully dive deeply into whatever subject is currently suitable to my making a larger impact at my organization, while also layering in that which I am simply interested in and passionate about.

I truly believe that it is possible today to learn more about a particular subject in a matter of weeks or months than in an entire four-year course of study at an accredited University. Yes, I believe I can develop more expertise about certain areas of business than people who have four-year degrees in that area, and I believe I can develop that expertise within a matter of months, if not weeks.

I can honestly say that I may learn more about leadership and management from 10 books (which I may consume in a matter of two to three months) than I learned about economics in my four years at Vanderbilt University. This is not a knock on the quality of education I received in college – I received a wonderful education from a first-rate university.

It’s simply a statement: I can regularly put in more hours to practical and relevant skills through books, audiobooks, targeted reading online, or through passionate debate with my highly intelligent colleagues than most people devote to an entire courses of study at a four-year institution.

In college, I was studying to produce As. In business, I study to continuously and dramatically increase my odds of success. Self-study with this intent is far more motivating and fun and has drastically increased the rate at which I learn.

College was merely the starting point, and my learning continues to accelerate. If you can receive the equivalent of a college degree in a particular subject area in a matter of weeks or months, then there’s no reason you can’t be among the world’s most educated – literally the most competent in the world, or close to it – within a few short years in a given area of study.

I am seriously suggesting that you continuously self-educate to the point where your knowledge parallels the learning of college professors in key subjects related to your work. No, that is not too extreme. It can be done during your commute, at the gym, during lunch, and on the job itself. Almost all of my learning is done on the job or while listening to audiobooks during my commute, at the gym, or while I’m doing the dishes.

It’s entirely possible that your co-worker on the marketing team has never read a book on marketing by a world-class marketing mind. Within a matter of months, you may be more “experienced” in your profession than people who have been working in the field for decades with only their narrow set of experiences to draw from. You, in turn, can turn to books and the crowd to absorb the perspectives of dozens of experts. If you learn with a voracious appetite, then within a matter of years, there won’t be any question about who the expert in your organization is.

I believe that the point at which you begin to develop competence is when you can read the insights of several brilliant thought leaders and disagree intelligently about what they have to say in specific areas. Or better yet, agree with directly conflicting advice – often both or many methods to achieve a result are workable. It’s like balancing the federal budget. From a very high-level (please don’t get entangled in politics here) the democrats want to raise taxes and continue spending. The republicans want to reduce taxes and reduce spending even more. Both schools of thought are practicable and have well-informed people agreeing with them. Both schools of thought have their obstacles and drawbacks.

Closely aligned with this concept of competence is the idea of practicality. Too many brilliant people have their heads in the clouds with a huge vision — or spend all their time learning but lack the ability to practically take steps toward achieving that vision. Focus your learning around those areas that you have the ability to impact with practical short, medium, and long-term action items.

If you are looking to develop competence, start with books. On your commute, while doing the dishes, or at the gym, begin consuming information on whatever subject you seek to become competent in. If you study for just 100 hours (maybe 10 audiobooks), you may find yourself more knowledgeable about a certain subject than folks who have spent years working in that field.

Moving past self-education, the process of developing extraordinary competence is vastly accelerated if you surround yourself with minds that also approach learning in this way. I had the privilege to begin my career at BiggerPockets learning from Josh Dorkin and Brandon Turner – these guys are among the most competent in the world in their understanding of the technology, media, and real estate industries. The three of us, for years, have read similar books and had hotly contested debates about new and exciting areas of business. I thoroughly consider Brandon to be one of the great marketers in the world and Josh to be one of the great technology entrepreneurs in the world. Almost all of their excellence was developed through relentless self-study and relentless practical execution to continuously learn in the field.

Our team here at BiggerPockets embraces this mentality and they too are world class in their respective arenas — constantly developing new expertise at all times. By demanding this from yourself and your colleagues, the cycle of learning accelerates and your knowledge advantage continues to grow.

2. Integrity

I think it’s imperative that you understand what it is that you value and how you want to be viewed by yourself and the outside world. And once defined, you need to operate with 100 percent integrity – 100 percent alignment with those values. If I’m not working with my absolute best intentions, at all times, for BiggerPockets’ members (you – the reader), for my boss, and for my co-workers, then I am out of alignment and will become sickeningly aware of an inability to act with complete integrity.

I relentlessly isolate and call attention to conflicts of interest  – my own, where applicable. Going a step further, I believe it’s important to be personally loyal to your colleagues, your boss, and the organization. That’s right – personal loyalty is often called out as something in conflict with the interests of the organization. I think that is baloney. If there is a conflict with being directly loyal to my direct superior and my direct reports and the company itself, then someone somewhere is acting without integrity.

And when that happens, I try to resolve it. There is no reason you can’t serve your boss, your peers, your customers, and your direct reports all with the highest level of integrity and all in harmony. If a conflict does arise, as they will over the course of your career, address it immediately and call attention to it. Or move on and create a situation where you are not forced to act against several parties best interests.

Competence is a prerequisite to integrity. It is impossible to act with integrity – more specifically it is impossible to serve the interests of your organization as effectively as possible – if you lack the competence to do so.

Failure due to a lack of technical skill, tact, or empathy often produces the same result as a failure due to a deliberate violation of trust. If I am not up to the challenge, it is my duty, and I am bound by that duty, to rapidly develop the skills necessary to fulfill the task or to hand it off to someone else who can.

If it is within my power to develop the competence to act accordingly, but I fail to put in the self-study to develop that competence, then that is a violation of integrity every bit as bad as being dishonest and sometimes worse.

Dishonesty is clear-cut, is straightforward for the organization to deal with, and theft or character violations can result in thousands or tens of thousands of dollars in losses.

But incompetence on the part of the individual can lead to losses significantly greater – in the form of the inability to act on future opportunities – and in many cases, it is significantly more difficult to tell whether someone is incompetent than if they were dishonest.

3. Be Thick Skinned, Yet Hyper-Empathic

No, I’m not saying that you should have thick skin in the sense that you shouldn’t care about other people’s feelings. You can and should deeply empathize with everyone with whom you come into contact with. You should learn from them, and like them (or at least some of their qualities), even those people with whom you never wish to associate with again.

Instead, you should have thick skin, a protective emotional barrier, with regards to what other people say to you and about you.

Never give offense, and never take offense.

It is amazing how people will hold grudges or throw away career opportunities due to petty slights, either given or received (and these can be real or perceived). I try to never demand an apology from someone else who has wronged me, and where I even conceive that I may have wronged someone else, I try to apologize immediately.

This is my definition of “thick skinned,” and I am by no means perfect at this. But I believe that this is a way of life and a good one. It’s a path towards more friends and fewer enemies and saves many potential troubles from escalating out of control. I’ve seen many other people ruin lifelong friendships, and even families split up out of an inability to man up and resolve a petty dispute with a sincere apology.

Who cares if I believe my behavior was in the wrong or not or what my intentions were? If my behavior offended someone for any reason, then I need to understand why that is the case and modify my behavior or my environment in the future to avoid continuing to give offense. And the first step in working towards that is something that is for some reason unfathomable to many – I apologize sincerely even if I’m don’t believe I did anything wrong.

This does not mean that I am a pushover and will simply agree with someone on an important issue to avoid conflict. Rather, it means that where a dispute is trivial, I immediately seek to ignore slights against my person, and empathetically modify my behavior so as to avoid giving offense to others unintentionally. Where a dispute is important, I stand my ground and stick up for what I believe in. It’s a matter of defining what’s important. How I say something is far less important to me than the message I try to communicate.

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4. Political Aptitude

I believe that a deep understanding of group dynamics is important not just for success in my career, but in all of life. I’ve been a part of organizations with political dynamics all my life, and where I am today is partially a result of how I navigated those political challenges. In my family, I knew who had the power over various aspects of family decision-making. On sports teams or social clubs, I knew who had the power and how to earn the respect and admiration of the group. I believe that you either understand the political reality of every group that you are a part of, or you fail and found yourself an outcast or forgotten in spite of personal merits.

A realistic understanding and empathy, not just with regards to individuals and their perception of you, but with their relationships with the group and each other, is critical to producing effective action in any organization and living in harmony with family and friends.

I’m not saying that you need to be calculated at all times when it comes to interacting with other people. This kind of political aptitude probably comes completely naturally to you when you are hanging out with friends or family – you simply know not to invite certain people who don’t get along to the same happy hour and know who likes Star Wars and who likes board games.

This kind of political aptitude is a core skill necessary to navigating life’s challenges outside of one on one dynamics.  It’s not enough to be excellent and to have high integrity. One must be excellent, have high-integrity, have thick-skin, and apply those core competencies to the power dynamics within any organization. If you have a great plan that will unquestionably produce a strong company result, then you must present it in a way that makes the people in power recognize it as such. If you fail to do that, you’ve failed to provide your company that opportunity.

And, if your organization is full of political challenges that make it impossible for merit to rapidly become accepted, you need to change organizations. I felt at my first job that the opportunities for advancement were limited by the group dynamics and rigid hierarchy of decision-making. The only way to make things happen at that job was to grab the ear of the key decision-maker (and my manager, my director, and the VP — all of whom stood between he and I). Only after at least five people, in hierarchical order, were convinced of an idea’s merit, would it be seriously considered for implementation. While I eventually left that job to join BiggerPockets, I understood that dynamic and worked through that system to the best of my ability to make things happen for the company’s benefit.

Be able to navigate the political challenges of your workplace with elegance and a clear understanding of group dynamics. You cannot execute with competence and integrity without the ability to mobilize your organization to action.

While politics is important for you at all times within other organizations, the job of a good leader is to remove political dynamics as much as possible from within your own organization. If political drama is holding back top talent, then you are reducing the probability of producing the most effective results.

I approach life with the assumption that politics are always within my control. I seek to understand and use the politics of any organization or situation I find myself in to my, my organization, and my peer’s advantage. But, as a leader, I also seek to create a situation where others in my organization do NOT have to have that perception, or are aware of those dynamics as much as possible.

Politics exists. In every organization. It’s your responsibility to navigate it effectively for yourself, and where you do find yourself in a position of influence, to call it out and help level the playing field for those who aren’t as adept in navigating group dynamics.

Related: The Secret the Rich Understand About Building Wealth

5. Self-Reliance

All of the above focuses on your interactions with others, and your ability to serve your organization with integrity, loyalty, competence, good humor, and to navigate the political challenges of your organization. But, perhaps paradoxically, I believe that in order to work with others with the highest level of effectiveness, you must possess a strong level of personal independence.

In my observation, people who are dependent on their organization, leader, or peers tend to play the game of business, particularly as months and years elapse, so as not to lose. Those who are self-reliant and self-confident in their personal lives, personal finances, and have other opportunities that they may pursue can act boldly and decisively, and they play to win.

When you act with any type of decisiveness, and particularly as you develop and demonstrate competence, the stakes rise, your accountability increases, and the risk of failure becomes steadily larger.

But, as you grow in the four areas described earlier, your odds of future success continue to increase as well. In order to act with integrity, you need to be able to stand up for what you believe in – and act boldly and decisively where necessary.

Financial freedom and the confidence to direct your own path makes you a better contributor to your organization over time than those who are too afraid of losing the security blanket that is their paycheck and positional authority within the organization to serve with integrity. And I believe that in perhaps devastating irony to those just getting started, the farther along you are towards financial freedom, the more effective you may become at your career.


Competence, Integrity, thick skin and hyper empathy, political aptitude, and self-reliance.

Again, I believe that these qualities are important to success not just in business but in personal relationships, family, and any social, religious, or charitable enterprises you may find yourself a part of in the future. But I call them out in this article particularly because these are some of the things that I believe have been particularly relevant in my own career.

I am by no means perfect or even approaching perfection in these areas. I have mastered few if any areas in which I’ve devoted countless hours to self-study, debate, and dialogue. I have no more than a cursory understanding of incredibly important areas of business (like psychology, behavioral economics, statistics, finance, marketing, sales, business development, and leadership and management). In spite of hundreds of books and perhaps thousands of hours of study in these areas, I’ve only scratched the surface. But, I’m getting better all the time, and each bit of knowledge gives me an increased edge in my career over those who haven’t taken the time to self-educate.

Every day, I find myself in situations that produce potential conflicts of interest. For example, I recently decided to begin work on a house-hacking book, a book to be published by BiggerPockets Publishing, LLC. This puts me in the position of negotiating with myself as an author, and with the company I lead. But, I try to point these conflicts of interest out where I can and find a solution that works for everyone and which is fair. I try to be increasingly aware of and upfront about these types of situations, which occur to lesser and greater degrees all the time.

I still take and give offense to others regularly, and am not able to forgive and forget the way I would like. But, I am working on this and am better than some, to my advantage.

I fail to understand political dynamics in many groups I’m in and am routinely surprised by the decisions that other people come to as well as which folks stand together and which find themselves in conflict. I’m also sure that as hard as I try, I am not able to completely remove the biases I have with regards to people that I come into contact with and make suboptimal decisions in part based on impressions that are not truly rooted in unbiased assessment. Yet, I recognize these weaknesses and seek to improve – I will never dismiss them.

And finally, I’m not 100 percent self-reliant and never will be. But I try to put myself in a position where I am a part of groups and relationships because I want to be there, not because I have to.

This was a long article, and is as much for me in putting my philosophy on paper as it is for you, the reader. I hope that you challenge my philosophy and tell me where I’m too earnest, and point out areas that I have neglected entirely that are critical to career success. And I hope that it serves you in getting you thinking about and adopting some of these principles, where applicable, to your own life and career.

Good luck!

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Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.