Winning and Success

I recently spoke to someone about the importance of understanding winning and success. Winning is something we’ve all come to know. The Patriots and the Cavs won and the Falcons and Golden State Warriors lost. You close the sale or you don’t. You get promoted to manager or your teammate does. Winning, is somewhat binary.

Success on the other hand is a more nebulous, and thus harder to define. In fact, if I were to ask you right now what success means you may or may not have an answer.

Furthermore, what you determine as success is going to be different than what someone else might view as success. Winning is not bad, neither is wanting success. It’s just important to define them for yourself and to know the difference.

The Average Paradox

The world’s most successful people tend to do things differently. Take any great artist/athlete/performer/entrepreneur and you’ll quickly see that they followed a different path than most of their peers which enabled them to achieve success and be unique.

Many of us want to be successful, to stand out and be above average. However, But being successful and standing out isn’t always easy, it means having the courage to do what you think is right even when it’s different than what almost everyone else is doing. Conformity brings comfort, which also is important. I came across a nice article that illustrated this point:

“We instinctively think we are above average. We don’t want to be average. Yet ironically, we want to be normal and have the same interests as most people do. We don’t want to be different and stand out. Having the same interests, routines, habits as everyone else ensures that we stay in the majority and are hence part of the ‘in-group’. But by design, we are setting up ourselves to be average.”

This describes what I like to call the average paradox. On one hand, our drive and focus on success means being exceptional and thus not just another average person. We want to succeed, do well and even stand out amongst the crowd.


However, we still want to be normal, and, have similar routines, and held to similar standards, which by definition, is average.

I have experienced this paradox myself. As a consultant, my job had a lot of ambiguity, even to the point where sometimes on a Friday I didn’t know where I needed to be the following Monday. In those moments, it’s easy for me to get stressed and think to myself, “if I only had a normal job..” The reality of that statement is that if I only had a normal job, I wouldn’t have gotten to do many of the things I really enjoyed about the job that I had!

There’s nothing wrong with being average. There’s also nothing wrong with striving for excellence. The only way around the average paradox is to pursue the things that are most important to our vision and values and acknowledge and accept the tradeoffs and opportunity costs that we must incur in pursuit of those values.

Being different is not always easy, but with patience and persistence, we can focus our efforts on becoming the person we want to be.

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How to use Self-Reflection to jumpstart your job search

I work with a lot of professionals who are looking to make job transitions, whether that’s from school to the workforce or from one job to another job. While some of my clients know exactly what they want to do, there are many others who know they want a change but are not exactly sure what kind of change they are looking for.

I think one of the most important factors to a successful job search strategy is a self-reflection of where you are today and where you want to go in the future. For some people, self-reflection and assessment is fairly simple, but for others, it’s ambiguous, so I wanted to lay out a step by step process for how to use a self-reflection process to identify where you are and where you want to go.

Identify what you’ve done

First, you need to understand what you have done and what skills and experiences you’ve achieved from your past work experience. This may seem like a simple statement, but it’s easy to get so laser focused on doing your job that you forget to take stock of the projects, tasks, assignments and actual responsibilities you’ve had as well as the impact of what you’ve done. Sit down, and literally write out all the things you did in your job(s) Go through your emails, your laptop, ask your co-workers or your friends, go through all means necessary to understand the scope of what you’ve done.

Identify your strengths

Once you’ve clearly laid out and understood what you’ve done and the valuable skills and experiences you’ve obtained, start identifying your strengths and the things that you are good at doing. Maybe you are a great communicator, or, really great with analyzing data and drawing insights. Everyone has a set of strengths that when utilized properly, make a contribution to your organization. Your goal in this exercise is to identify the ones you bring to the table. Same as last time, write these things out so you can start to see what strengths your bring to the table.

Identify your interests

Additionally, you’ll also want to identify the things that you enjoy doing. While not every job will have 100% enjoyment, it’s important to know the types of things you like to do and want to do. This is because many of us are more engaged and excited by things we enjoy doing, and we tend to exert my energy, enthusiasm and are equipped to do these things well.

So why do you need to do all these things? In a very simplistic view, when you look for a job, you’ll probably want to look for jobs that have opportunities for you to use your experience, strengths, and things you enjoy doing.

Identify the future

Once you understand the present, you’ll want to identify what’s in store for you in the future. What type of job do you want to do? The goal here, is to develop some hypotheses about different jobs you think you’d like. The goal here is not to be 100% correct, but rather, to come to a few hypotheses about what potential paths might be desirable for you to pursue. So, how do you go about doing this?

Research – Using your skills/experiences, interests, and strengths, start looking at future jobs or roles and evaluate if they are a good fit. Sites like LinkedIn and Glassdoor are a great place to start. Does the job you’re evaluating make use of the strengths and experiences you bring to the table? If so, that might be a potential good fit

Network – Talk to people who are already doing the jobs you might be interested in. Get to know what their day is like, and get to know the strengths they use everyday and what they like/dislike about their job

Learn – Learning something new has never been easier. Take an online class, watch YouTube videos, or read articles to determine if that job you think you might want is something you want to pursue.

To summarize, here’s what you can do:

  • Write out your past skills and experiences
  • Identify your strengths
  • Identify your interests
  • Identify a few paths you want to pursue

If you can do these things, you will be ready to start your job search on the right foot.

Pro Tip: If you really want to do some serious self reflection, here are two resources below that might help

Myers Briggs Test – A test to determine your personality type, and how you best engage and interact with other people

StrengthsFinder – A tool developed by Gallup Consulting to help people understand their unique strengths, and to help them identify opportunities to use these strengths