Connecting The Dots Looking Backwards – Deconstructing My Career




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You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. – Steve Jobs

I’ve always been a big believer that every experience acts as a stepping stone to your end destination, however momentary it may be. I tend to think of the destinations as I go more like waypoints along a much longer journey. Each arrival is only a snapshot in time and after a momentary pause acts as the starting point on the way to the next waypoint.

Sometimes there’s a real awareness of how decisions and experiences will connect in the future; but most of the time I’ve just had to have a little faith, trusting that somehow everything will ultimately connect.

I have tried and failed at a lot of things. When people only see where I am today, they don’t know that. Nor do they see that despite my nature to be extremely premeditated, this path hasn’t always been clear. As Steve Jobs says in his quote, I can only now connect the dots looking backwards.

Many of you in comments or through private email messages have asked me how I’ve managed to grow my career so quickly. Everyone wants the SECRET SAUCE!

But it’s only now, after ten years on my career path, that I can look back and identify what helped me reach the C-Suite by my 30th birthday.

A jungle gym scramble is the best description of my career, I could never have connected the dots from where I started to where I am today. It’s better to think in terms of a career jungle gym than a career ladder. – Sheryl Sandberg

Ten factors come to mind, all of which played an essential role in how I got to where I am today. You could also say that it was these same ten things that have allowed me to grow our household income to the top 2% in the US

#1 Be Not Afraid to Ask

One of the biggest roadblocks that I’ve witnessed holding people back is the fear of rejection. No one likes to hear the word NO…but you cannot be afraid of hearing no! Instead, you have to remind yourself that the worst that might happen is that “they” say no. But more importantly “they” might say YES.

You can’t get what you don’t ask for.

People that ask for more money tend to make more money.

My career started by suppressing the fear of rejection. In a spring semester class of my second year in college, we had a guest speaker. He was the CEO of a multi-billion dollar oil company. This guy was fascinating, and by the end of the presentation, I knew I wanted to work for his company.

This CEO was leading a second generation family-owned business preparing to hand over the reins to the third generation. He had started out driving a truck to deliver fuel to customers, gone out on his own to gain experience outside of the family business, and then come back and bought the company from his dad over time. From 1990 to 2006 he built the company up from $50M in revenue to over $3B.

I wanted in!!!

At the end of the presentation, he asked the class if we had any questions. To my surprise, I was the only one raising my hand. I peppered him with question after question, and he seemed to enjoy this private conversation we were having in front of the rest of the classroom.

Class ended at 8:50 am, and the CEO said he would hang around for a few minutes if anyone had any other questions. As everyone else in the class raced for the exit, I headed straight for the CEO. I thanked him for his presentation and his willingness to indulge me in my interrogation of him in front of the entire class. I then proceeded to tell him how impressive and inspiring his story was.

I had one last question to ask. I wanted to ask him for an internship at his company.

Was it uncomfortable? Yes. Was I nervous? Yes. Was I excited? YOU BET YOUR ASS I WAS!

I had no competition. Although rejection is always a possibility, I was stoked that he might just say yes. So, I stopped stalling and asked him if his company ever offered internships, and his reply was “We have a whole team dedicated to that.” This was all moving in the right direction. Next, I asked him what types of internships were available (like finance, marketing, and so on). I knew I was in with his next response: “Whatever you are interested in.”


He then proceeded to give me his business card and told me to email him later that day so that he could put me in touch with the HR department to set up an internship. That’s how I got my start in finance. And I ended up working for that company for nearly five years.

The funny thing I learned after starting my internship was that I was the first intern the company had ever had and they did NOT have a whole team dedicated to interns. My direct boss, who is still a mentor to this day, later shared with me that he was TOLD he was getting an intern. When he pushed back saying he didn’t have money in his budget for an intern, he was told that Frank (the CEO) was taking care of it.

All because of a simple ASK!

#2 Fake It Until You Make It

CAUTION: To be successful you need to pair this with #3 and #4 below. You will also need a dash of #8 as well.

A certain behavioral psychology concept says if you want to think and feel happy, positive, and enthusiastic, then you must act happy, positive, and enthusiastic. In other words, act “as if” (fake it) and your reality will follow your behavior (you’ll make it).

Let’s say someone asks you to do something. You know it’s possible, but you have yet to tackle a similar project. If you are aware of your capabilities and understand that resources exist to help you accomplish what is being asked, commit to the project with confidence as if it’s no big deal. 

I am not telling you to go out there and brashly write a check that can never be cashed because if this is the case, it will simply bounce. Making blue-sky promises you can’t deliver on is not a good way to build up career capital.

What I am saying is that it’s okay to stretch your skill set and knowledge base. Sometimes you’re in a meeting with people talking about things you have little experience with, but maybe you have read about the topic. Instead of showing your greenness (is that a word?), jot down a few notes and questions to look into after the meeting (that doesn’t mean you don’t ask questions in the meeting, but it may not be the best forum for a deep dive). Then go out and learn what you need to stretch into this next project and phase of growth, making yourself more valuable.

We live in a day and age where information is at our fingertips. Lack of resources is no longer an excuse. Anyone trying to use this excuse is the one lacking –  lacking the skill of being resourceful. What can’t be learned these days in a simple Google search, in a book at the library or on Amazon?

Note: Be careful here with the promised timing to deliver. Consider the time you think it will take and double it. You can always deliver the project earlier. Under promise and over deliver! Another tactic that has worked well for me is to play up the complexity of the project. Instead of committing to a deadline on the spot, I might instead tell them I would like the next day or two to evaluate the project completely and that I will then circle back with a timeframe for delivery.

I truly believe that this can be a philosophy that can make or break a career, so use it very strategically.

An excellent example of how I used this philosophy in my career was when I was trying to make a transition from corporate finance over to digital analytics. At the time I was working for a $2B company in the action sports space, which had a $100M eCommerce business. The world of online commerce fascinated me, and so I began a year-long pursuit to securing myself a spot on the eCommerce team. The first thing I did was volunteer to get more involved on the finance side of this business. I partnered with the Senior VP of this business and did everything I could to help him.

At the same time, I found the best eCommerce blogs I could and even ordered a few books on the topic. I taught myself a lot about the eCommerce business with a specific focus and emphasis on the analytics side of the business. I learned all the lingo: average order value, conversion rate, PPC (pay per click), up-selling, cross-selling, split testing, lifetime value, COA (cost of acquisition), organic vs. paid vs. referral vs. direct traffic, email marketing, social media marketing, SEO, attribution, affiliate marketing, google analytics, etc.

One of the best investments I ever made was the $40 I spent on Avinash Kaushik’s 2 books “Web Analytics: An hour a day” and “Web Analytics: The Art of Online Accountability and Science of Customer Centricity.” These books and his blog were GOLD! I bought a half dozen other books and read a dozen other blogs, but Avinash had it all, at least from the angle I was pursuing.

After six months, I started asking if I could get an invite to more operational team meetings, which is where I got to “talk the talk.” I had read enough to sound knowledgeable on the topic. I started to throw out ideas on how we could use analytics to increase our average order value or tests we could run to increase conversion rate. I volunteered to undertake a project to figure out what the lifetime value of a customer was so that we could figure out what our cost of acquisitions could be.

Around this same time, it was announced that a new digital analytics team was going to be created, which was going to report under the new SVP of digital marketing and analytics that we had just hired. This was my in!

Somehow I was able to convince the CFO of the Americas, someone I looked to as a mentor, to help me get a chance at being a part of this new team. It worked, and I got a meeting. Two weeks before the meeting, as I continued to read everything I could on the analytics side of the business, I came across an article published by Harvard Business Review titled “Advertising Analytics 2.0“. By this time I had been eating, breathing, and spending every free moment obsessing over this space. I went to that meeting with confidence and excitement. We had a great conversation, and it ended with “we need to have a guy like you on this new team.” I had officially secured my spot as a founding member of this new team.

Later, I further capitalized this skill set by developing a very lucrative side hustle. Read how I took these skills and started a consulting practice on the side to continue refining these skills.

I do want to add an adjunct to this principle: GIVE BEFORE YOU GET. Note that I did six months of intense study, extra work and offered to be of help before there was any guarantee of reward for myself.

#3 Be Resourceful

Even taking into consideration all the extant problems of the world today, I still believe we live in the best time in history. Admittedly, there is income inequality, with the divide between the 1% and the 99% larger than ever. But…while the rich keep getting richer, so do the poor. Take a step back to absorb that for a moment. There is no doubt in my mind that the quality of life is exponentially better today than 100 years ago, for everyone, at all levels of wealth or poverty. Shoot, life has only continued to improve for the entire three decades that I have been alive and if you don’t believe me, check out this post.

I don’t pretend to speak for anyone else, but the overall trend I see looks pretty darn positive.

Most importantly, we live in a time where information is at our fingertips. Anyone with a smartphone holds more access to more information than the President of the United States did just 20-30 years ago. All in the palm of your hand, at a moment’s notice.

Do you realize how LUCKY you are?

I honestly believe that it has never been easier to be successful. Those complaining that they lack resources really only lack resourcefulness. Truly, if there is a will, there is always a way, and ample tools available to get from where you are to where you want to be if you will seek out those tools and use them. It doesn’t matter where you start in life. Trust me, I know. I pretty much started at the bottom of the barrel.

Of the infinite tools at our disposal, the one that changed everything? THE MOTHER F*@%& INTERNET!!!

The internet has allowed for a new dawn and unprecedented access to both people and information:

  1. Google – Thank you, Larry and Sergey; you changed the way people access information.
  2. Amazon – I can get any book imaginable, in my hands within two days via Prime.
  3. Blogs – There’s no topic you can’t find an excellent blog on.

Without the internet, I doubt I would be where I am today. Via this tool, I know that if I apply myself, I can learn whatever I need to in order to get anything done. Any of us has unprecedented access to the brightest minds…EVER! If there’s something I want to do, or a skill set I want to learn, someone else out there has probably done it first, and you bet I will seek out their knowledge to leapfrog me ahead to where I want to be. 

With a little curiosity, initiative, and determination any of us has all the resources ever needed to make a dent in the universe. Want it, and go get it. Be the one who finds the solution. That is resourcefulness.

#4 Always Be Learning

The most successful people in the world are perpetual students. Learnings translate into earnings. The more you learn, the more potential you have to earn. Too many people think that their education stops when they graduate from college (some even after high school). In reality that is just a warm-up for a lifetime of expansion through learning.

A formal education will make you a living; self-education will make you a fortune. – Jim Rohn

For many, any type of classes stop with graduation. But even worse, 42% of college graduates never read another book after they leave school! I truly feel bad for them as they are doing themselves a huge disservice. Books give us the ability to experience 1,000 lifetimes beyond the one we are individually limited to experience here on Earth. Talk about leverage! All of the world’s most significant mistakes and incredible achievements are right at our fingertips to learn from. 

I am a big fan of actual books, and am on my way to building a library for the 250 books (99% non-fiction) that I have read since 2011, when I embraced this concept and committed to an intention to improve both personally and professionally. I’m leaving space for the 50 more books per year I continue to read. But books are not the only learning tool we all have for learning. There are blogs (hey there!). YouTube. Podcasts. Audio Books. Via any of these channels, I can read-watch-listen to the wisdom and information of the best and brightest among us, and add their knowledge to my own. 

Specific to my career, two things I have done consistently better than the majority of my peers, which both fall into the category of “always be learning:”

  • Invested a lot of time learning new things.
  • Invested a lot of time improving current skill sets and developing new skill sets.

Learning makes me prepared, and being prepared allows me to be “lucky,” as in right time, right place kind of lucky, for opportunities both known and unknown. (More on that in #10.) 

Of course, most importantly, learning makes anyone a better and more interesting human being, but since this is a blog about money, I’ll show you an example of how learning can translate into a high level of earning.

Remember that internship I got at the oil company? I joined the finance team and quickly found out that Excel would be my primary tool. However, the mad skills I thought I had? Nothing to write home about. I watched the senior financial analyst who was training me do magical things in Excel. What I brought on day one wasn’t even 1% of what Excel could do.

I had an epiphany: I realized that if I could get my Excel skills in the top 5%, I would have a highly desirable skill set, one that would allow me to add a lot of value to an organization, and thus command a premium in compensation.

Coincidentally, there was a three-day Excel seminar nearby in a couple of weeks. I was determined to surpass the skills of the senior financial analyst I was working with, and signed up. After spending 36 hours nerding out at the seminar, my biggest takeaway was that the only limitation to what I could do in Excel was my imagination to conceive it. I also learned that the average person in the workplace was only using 5% of Excel’s capabilities. For professionals in the finance field, this stat was a bit higher at 35%.

The company I was interning for paid for the seminar, but I made a further $1000 investment in another, more comprehensive, program they had for sale at the event (a lot of money for a college student).

I spent the next six weeks devouring the deeper program and immediately started looking for ways in my job to apply what I was learning. Since it was such a significant investment, I wanted to find a way to get paid back for the program. So a few months later I tackled a project to automate the generation of the financial statements, which was previously completed with a very time-consuming manual process. I was successful and created a process in Excel that used Macros with a click of a button to generate the financials. Everyone was amazed!

That’s when I asked to be reimbursed for the program I had invested in. Without hesitation, I got an immediate yes to my request, with the idea that others in the department could use the same program to improve their own skills. Guess what? No one else ever used that program. (See #6.)

I continued to hone my Excel skills, and I believe that the skills I learned at the seminar and expanded on by myself earned me an additional $15,000 when I got my official offer to join the company after graduation. I started my career as a financial analyst making $63,500 right out of school, while all of my college friends in my major got $45,000 to $50,000.

You need to know that those who never stop learning will always have the knowledge edge. And you want every advantage you can get in this life.

Go to bed smarter than you woke up. – Charlie Munger

#5 Develop a Rare and Valuable Skill Set

If you want to have a career and not just a job, then obtaining a rare and valuable skill set is critical. If you can only do things that anyone can do, then don’t expect the fancy titles or the big bucks in your future. Specialize. Even better: choose something where you can excel to the top 5% of the field.

Can you guess the rare and valuable skill set I decided to pursue?

Ok, maybe I set you up for that one because it’s not Excel. Yes, Excel has played a pivotal role in my career, but it’s just a tool, one of the multiple tools I have utilized through my career to deliver a lot of value leveraging DATA (the cool kids refer to it as Big Data these days, thus the all caps).

My facility with DATA is my true “Rare and Valuable” skill set. Yep, I have built my career around being able to work with data, and I learned to be agnostic as to the source and structure, meaning that I can pull in and analyze data from almost any source. If I had to boil down to four words what my skill set allows me to do with data, they would be:

  • Consumable – I turn raw data into information that can be easily understood.
  • Insightful – I filter out the noise and draw out the insights.
  • Actionable – I make the data actionable.
  • Automatable –  I make it automated when appropriate.

To me, information and communication is where the future lies, which is why I’ve positioned myself at their intersection.

I guess you could also say that I am a bit of process optimization expert as well, which means that I am good at evaluating current processes (usually very manual and labor intensive) and then redesigning and automating them. An example would be the reporting process that was in place when I joined my current company four years ago. It used to take them three to four weeks, with seven to eight different people touching some piece of the reporting process (and data), to get monthly reporting out.

I was able to cut this down to one person and one day by leveraging technology to automate most of the process. Removing all those unneeded touch points freed up $60,000 per year worth of man hours and provided information in a much more timely manner by which to manage the business.

An adjunct to this precept is to know what your rare and valuable skill set is, and be able to communicate it, especially in terms of the benefit it offers another stakeholder in a project. This is true whether you are happy where you are or whether you are out job-hunting. Be prepared to communicate clearly what it is you do, and why it is valuable. (See #7 below.)

#6 Hustle, Hustle, Hustle

First Part Time Job Meme

In my post about the reality of the overnight success I had the following to say (and it has everything to do with Hustle):

My guess is that many of you who read this blog believe like I do that you always have to be “on” and “productive.” You’re a SERIAL ACHIEVER who has a hard time shutting it off and shutting it down. You always have to be learning. When you’re not learning, you’re taking action and applying what you’ve learned.

You’re almost always doing one of the following:

You’re Producing.

You’re Creating.

You’re Planning.

You’re Teaching.

You’re Taking Massive Action.

Rinse & Repeat!

It’s what we know will get us everything we desire in this life.

People like us realize that if we don’t go to work building our dream, we’ll end up living our whole lives building someone else’s dream. We are motivated by the fact that we can and will design the life we desire through pure AMBITION if necessary. We will overcome any lack of innate talent by out-working and out-learning those who are naturally more gifted than we are.

We understand that compound effort is just as powerful as compound interest.

After writing the post linked above,  I wrote a follow-up piece expanding on this idea of out-working or HUSTLING your way to SUCCESS:

Have you ever heard of the Latin phrase “Fortitudine Vincimus?”

It translates to “by endurance we conquer.” It’s a motto I’ve internalized while building my career and wealth. It’s a motto I encourage everyone to adopt if they genuinely want to experience the magic of exponential results. It is endurance (i.e., time) that makes the power of compounding so magical. This is true for investment of effort just as it is for investment of money.

You don’t have to be the smartest or most innately gifted to succeed. Any normal person can gain an edge by out-working and out-learning the naturally gifted. To me, there is no such thing as competition. Most people are pretty lazy, which means that the top is never crowded.

Nothing in the world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. – Calvin Coolidge

As I string together the philosophies that have landed me where I am today, a couple of things are becoming apparent to me. First of all, the consistent work it took to create this blog while building a demanding career is proof of my ability to hustle! But also, as I link back to previously published posts, I’m noticing that these ten concepts appear multiple times, in multiple ways, throughout my archives.  As I revisit the last ten years of my career, it is only now becoming apparent how all ten concepts have been consistently woven through my thoughts and trajectory, both personal and professional. Interesting.

Yes, it has been a dedicated and concerted effort. But I’ve always been willing to live my life like most won’t for a few years (okay, maybe a decade plus, but you get the point), so that I could live the rest of my life like most can’t. I believe this can work for anyone.

#7 Sell Your Value

To have a rare and valuable skill set is vital, but being great at what you do and being noticed for it are two different things. You have to be good at tooting your own horn from time to time. It’s all a part of the game. Whether you think you’re in sales or not, you are in sales! You have to be able to sell yourself and your unique abilities and contributions to the key players within the organization you work for.

This is equal parts marketing and office politics.

It’s not just about being the best at what you do. You need to play the politics game. When I say “game,” I don’t mean anything underhanded or manipulative, but rather a recognition of the power dynamic that is part of any organization. You need to identify the key players that can have an influence on your career and you need to get their attention. Figure out what you can do to make their lives easier and to make them look good. Demonstrate how your rare and valuable skill set makes you invaluable to them.

Your goal is to help as many of the influencers within your company get what they want, so in the end, you will always get what you want. Be so good that they can’t ignore you!

You can have everything in life you want, if you will just help other people get what they want. – Zig Ziglar

To do this, sometimes you’re going to have to take some risk and break the rules from time to time, especially in bigger companies. The reality is that you probably don’t have direct access to the key players at the beginning of your career, so you have to find a back door. I admit to getting my hand slapped from time to time, but in the end, it’s always been better to ask for forgiveness than for permission.

Note: I am not saying to go above your boss from day one, but if your boss is holding you back, you will either have to go around him or her or stagnate in your career.

The last thing that I will add here would be to take advantage of every opportunity you can to translate your contribution into top or bottom line results. Always be looking for ways that you can add to the success of your employer, either in gross revenue or in greater profits. Or both!

#8 Develop a High Sense of Self-Awareness

You need to know what your strengths are and double and triple down on those things. You need a keen sense of self-awareness to figure out what your rare and valuable skill is (#5 above). What can you offer the world that will put you in the top 5%? Once you identify this, you need to go all in and HUSTLE your ass off.

What are you naturally good at? What are your weaknesses? Know the answer to both of these questions. This is the time for introspection. If you get stuck, ask your trusted inner circle what they think you’re good at and weak at. You can use a personality test such as the DISC or Kolbe. Once you have your answers, hustle to your strengths via extra training and self-education.

I think Gary Vaynerchuk sums this up well in the 3-minute video below:

#9 Be In It For The Long Game

Too many people quit too early!

We live in an instant gratification society. When the results aren’t immediate people quit.

It’s stupid to start, give it your best shot, waste a lot of time and money, and quit right in the middle of the Dip.

The Dip is the uphill battle you face after your initial excitement and early success wear off when working to master something new. Take starting a blog for example. What percentage of people do you think stick it out through the dip? According to a 2009 article in The New York Times, 95% of all blogs are abandoned by their authors. Most quit within six months. Now some of those authors were right to quit because they were not willing to pay the price for success. But some of those authors frankly gave up too soon. They gave up inches within riches. Most of the effort in any endeavor comes in moving from inertia to motion. So if you can just get your metaphorical ass up off the metaphorical couch, you’re more than halfway there! Stick it out – be in the minority that persists!

The fact that most people give up too early is why you never really have to worry about the competition. When it comes to success, Seth Godin says “the entire process is built around many people starting while most people quit.”

The reason I am such a fan of the book “The Slight Edge” is how it speaks to the concept that improvement is not linear:

For the beginner, improvement will be linear, but the real gains happen when compounding kicks in. It doesn’t matter if it’s your wealth, your health, or your career. Real progress is experienced as a lot of little changes that by themselves seem like nothing material, but which over enough time compound to HUGE gains.

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.” – Bill Gates

Sometimes the progress we make doesn’t seem visible or worth the effort. But over time it starts to add up and compound. Think about it this way: imagine you are trying to improve just 0.3% per day. In a day or two or even a week, that may not be a noticeable amount of improvement, but it adds up to almost 1% improvement every three days, and by the end of the year you will have improved over 100%.

Will you give yourself enough time to experience the exponential gains? Will you persist?

Real progress is experienced as a whole lot of nothing for what seems like long stretches of time, followed by exponential step-ups, and those step-ups seem like they happen overnight. But in reality, they were 10-20 years in the making.

Success is a long game: stay in it.

#10 Acknowledge That Luck Always Plays A Role

If you spend 10 years on one path you’re more likely to get lucky than if you were to spend 2 years on five different paths. – Wall Street Playboys

Luck can be something that happens to you. For example, winning the lottery. Being born in the USA.

But that’s not the kind of luck I’m talking about.

I’m talking about the kind of luck you create. Yes, you can create your own luck. You may not be able to control all aspects of luck, but through your actions, you set yourself up to be lucky. There’s a reason that I’m closing this with luck because without checking the boxes for the previous nine points, luck isn’t even a factor.

To me, luck is just a fancy word for opportunity. We are surrounded with opportunity, but it passes us by when we are not prepared. Then we blame being unlucky when it does. That is an excuse and cop out. It’s kinda lame if you ask me.

If you want to be lucky, be prepared and luck will find you!

#11 The Secret Sauce

You’ve read this far, so here is the Big Reveal: there really is a secret sauce. I’m going to give it to you right now. Ready? Here you go: Do #1 – #10. Then keep doing them. And doing them. And doing them. Endure. Persist. One day you will look up and see how all your own dots connect in an incredible way.

What are your top ten – different from mine? I’d love to hear about your success stories. Let me know what works for you, and how you’re doing – I’m rooting for you!

– Gen Y Finance Guy

Gen Y Finance Guy

Hey, I’m Dom - the man behind the cartoon. You’ll notice that I sign off as "Gen Y Finance Guy" on all my posts, due to the fact that I write this blog anonymously (at least for now). I like to think of myself as the Chief Freedom Officer here of my little corner of the internet. In the real world, I’m a former 30-something C-Suite executive turned entrepreneur turned capital allocator. I am trying to humanize finance by sharing my own journey to Financial Freedom. I believe in total honesty and transparency. That is why before I ever started blogging, I decided that I would share all of my own financial stats. I do this not to brag, but instead to inspire motivate, and also to hold myself accountable. My goal is to be a beacon of hope, motivation, and inspiration, for you, the reader, by living life by example and sharing it all here on the blog. My sincere hope is that you will be able to learn from me - both from my successes and my failures! Read More



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17 Responses

    1. Hey Garrett,

      It has been a long time. It is great to hear from you and I hope all is going well for you as well up there in NorCal.

      I will hit you up next time I am in NorCal.

      Glad you found it inspiring!



  1. Dominic, Congrats on your promotions and success. I hope the following is not too long but you made me think. I am 51 and have worked my way up and manage a significant program and team. I’ve seen or experienced everything you mentioned in this post, in one way or another, and know you are right about all of it. You are correct that most people are lazy and competition is rarer the higher you go. Anytime an employee asks me if they can spend money to attend some seminar I say yes, because I like to see the ambition and it happens so rarely. I would actually have categorize myself as lazy relative to you and to plenty of people higher than me in my organization and industry. I have currently stepped back one level to have an excellent boss and work on a particular project, because I’ve reached a place that I can be choosy. But I’ve done well, including being a national VP. I was also briefly a senior executive but I learned I didn’t like it and was not great at it, so I went back to my niche (with an even higher salary). I have been kicked in the ass a couple of times but got right back on the horse and got more responsibility and more money. With the pedigree I’ve built I am confident that can get any job or consulting gig in my field that I really want (a couple of times I have not gotten the job I explored but I got called back by the organization and offered even better ones).

    I credit the compounding of simple disciplines over time, coupled with massive effort when important opportunities come along; not being a jerk; taking the risk to be in a revenue-generating niche versus support fields and thus having higher compensation; not sticking around too long – I think 3-5 years in any one position is about right for my field. Less than that too many times and I look like a job hopper. Longer than that and I either start to look like a lifer and I notice I start to sound negative and entitled – that never ends well; only associating with quality brands, both for leading organizations and with quality teams within them; living in large cities with lots of opportunities; only working for organizations that have abundant resources to do the work and compete; quietly cultivating relationships with leaders who are not my boss and could be positive references for me when I move again; saving and investing nearly half my income so that I am bullet proof and have maximum options, etc. Plenty of people have done better than me but I’ve done more than most in my field and my own secret weapon has been this sort of quiet strategy to position myself for the next thing.

    One challenge is knowing the difference between “the dip” and when to stick it out versus knowing a situation is either too boring or a poor fit and getting the hell away from it as fast as possible. Looking back, though, my 3-5 year tenure rule fixes most of those problems. Thanks for the thought-provoking posts and best wishes. Anyone driven enough to follow even 75% of your advice above is going to advance further than they can probably imagine. It’s clear to me that, whatever reasons, 95% of people seem to give little thought for their futures and can’t be bothered.

    1. Hey Mark,

      First, thank you so much for your thoughtful comment. You can never leave too long of a comment, one of the things I look forward to most when I put out a blog post is the dialogue that happens down here in the comments section with people like you.

      I appreciate the confirmation and feedback that you have experienced in your own career. It’s interesting that you took a step back after wearing the executive hat for a while, but that goes back to self-awareness. That level of self-awareness to take a step back like that had to go a long way with enabling you to go back to your niche AND earn more money.

      Your quote:

      “I have been kicked in the ass a couple of times but got right back on the horse and got more responsibility and more money.”

      I think if I were to add an additional item, it would be resilience.

      I also really resonate with this quote (very much Slight Edge philosophy):

      “I credit the compounding of simple disciplines over time, coupled with massive effort when important opportunities come along”

      I would be interested to hear more about what line of work you’re in?

      The idea of this optimal 3-5 year tenure is an interesting thing to noodle over a bit more. Thank you for your thought-provoking comment.



  2. Great article full of important, valuable content! You have clearly leveraged everything you listed, which is truly inspiring! I shared part on instagram with pleasure, as it struck me so powerfully. Thank you!

  3. Great blog, a lot of it felt like reading an autobiography. In fact that oil company you interned at sounds like one of the companies that owned the division I was running when I early retired a couple of years ago. I guess where our stories diverge is I got tired of the Fortune 500 quarterly craziness and recognized that the parts of my job I liked the most weren’t the core parts that demanded most of my time. So I walked away with more money than I’ll ever spend and designed some side gigs that are nearly 100% in my favorites zone. I’m pretty happy with a couple of days a week of enjoyable and challenging work and a half dozen volunteer gigs like chairing a college board and running a large charity foundation plus a bunch of hobbies and travel. It isn’t close to as intense as the corporate world but I haven’t missed the drama at all. I thought every single thing you said was on point and those were the keys to my success as well, although I never stated them that well. I hope people take those to heart. It isn’t hard to succeed at a super high level If you do those things.

    1. Steveark – Thanks so much for the comment. I will send you a private email with the company I worked at to see if the world is indeed as small as it seems sometimes. It sounds like you have really found your sweet spot. At this point, I currently like more about my job than I dislike, but I am actively working towards putting myself in a situation to walk away at some point to spend 100% in my favorite zone like you. I probably spend about 65% in my favorite zone.



  4. Wow. Really appreciate how you realize your steps in hindsight. Your #1 and #7 really speak to me. I think your #1 (ask) doesn’t work for most people, because they only see what they want instead of what meeting the other side’s wants. That ties directly to #7, because without the value that CEO saw in your questions and interest there would have been no reason for him to hand you his card and open this opportunity. You showed him the ‘win-win’.

    Also like your point about ‘everyone being in sales’. This was pointed out to me by a mentor, when he relayed a discussion he had with a sales staff member who whined, “you’re lucky you aren’t in sales!” My mentor then pointed out that our jobs were actually ‘sales jobs’ (consulting), because every day we could be removed and sent away for any, or no, reason. We had to show ‘value’, and sell the client(s) on why they were paying a premium.

    Thanks for laying this all out, very thoughtful post!

    P.S. – I dig it when you get enthusiastically buckwild in your word choices!;-)

    1. JayCeezy – Glad someone enjoys my occasional colorful language. You can always tell when I may have enjoyed a few cocktails in the process of creating a piece of content. To be honest, I actually think my writing gets better and more engaging when I am slightly buzzed. At the very least I tend to have a little more fun with my writing and am more liberal with my word choices 😉

      Your quote:

      Really appreciate how you realize your steps in hindsight.

      The process of introspection and reflection has been one of the most valuable things this blog has added to my life. It has forced me to be a better thinker and to pluck lessons from my own experience in a very systematic and documented way. The act of typing then solidify’s and memorializes these lessons for future reference and for sharing with others.

      Thank you for taking the time to read my longest post to date. I had contemplated splitting the post into two parts to reduce the 17 minute read time, but didn’t like the idea of splitting up the content. My hope is that it would be an interesting and engaging enough read that those that really wanted the takeaways would invest the time to read the entire thing.



      1. LOL! We are both fans of Tim Ferriss, and your comment reminded me of this quote of his from ‘Tools of Titans’ when he is describing his writing process:

        “Pro tip: writing quality does not improve after the third glass of Malbec.”

        1. Note to self…stop writing after pouring the 3rd drink 🙂

          Yes, I am a huge fan of Tim Ferriss. I still have one section of the ‘Tools of Titans’ to read through. But overall, I liked the short form content.

  5. That’s one mad post. All those points are spot on. I’m also always trying to learn new things and getting out of my comfort zone. Complacency kills. I agree with the comment about taking massive action. Too many people suffer from analysis paralysis and end up doing nothing. Wishing you continued success!

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