Being the Worst player on a winning team vs. the Best player on a losing team

Ted Murphy of IZEA just asked this question via twitter:

Very good question and I wanted to elaborate about this.

My first response to Ted was that it really depends what game we’re playing, what the perks are of winning and what the risks are of losing.

I grew up playing basketball and my dad always took me into the inner city to play on teams with the best players.  At practice many times I often got whooped, but I learned and grew.  I eventually became the leader of my region in scoring in high school on a winning team and even played college basketball for a year.  What I realized however is that there has to be a balance between the two concepts to really reach your full potential.  Each concept has different perks which can add value to your personal development in business, sports and life.

Being a nobody on a winning team Perks

  • You get to see first hand what it takes to win and how the leaders of that team carry themselves.
  • You surround yourself and make contacts with the right network of people.
  • You get to reap the rewards of being a winner, which can be extremely fruitful even for the nobodies.

Being the best on a losing team perks

  • If your goal is to become a great leader, sometimes being the best on a losing team can give you the ability to practice leading and really hone your skills so you can eventually be a leader on a winning team. You may even be able to turn your losing team into winning one.  For example Michael Jordan went through many losses and took the game winning shots and missed many times.  However he learned what that responsibility is like and how to focus and take control in crunch time and turned out to be the greatest player ever in history.  Being on a winning team with other stars you may not get the chance to take that winning shot and will miss out on that aspect of personal development.

When looking at this concept in relation to my start up and business career expectations….

If GroupTable were to get venture funding and the investors brought on an experienced CEO to run the company and my equity & position in my own company got diluted immensely, I would be ok, or even embrace this as long as I thought the team I co-founded would win.  My business partner Scott Wall often says it’s better to have 1% of $500M than 100% of nothing.

However there will come a point in my business life where I have been on enough winning teams to know what it takes and will want the responsibility to lead my company to success.  Even if I make mistakes, which any successful person has done, you will eventually learn how to handle those situations and excel…just like Jordan did.

Well…even if it’s not quite “Just like Jordan did”, you can at least reap great rewards when you learn to focus and control risk in tough situations like he did.

What are your thoughts on this issue…Which team would you rather be on?

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  1. Hmm…That’s a tough one. I think you pointed out the advantages and disadvantages very well. There are many perks to being the worst player on a winning team as well as being the best player on a losing team.

    As you mentioned in your post, you can learn alot from watching others. In fact, that’s how alot of sports figures and CEO’s of different companies start off. In the sports world, they would call this riding the bench. In the business world, its referred to as an internship.

    I did an internship in college with Pat Cavanaugh, CEO of Cavanaugh Marketing Network, and I would have to say that I was the worst player on a winning team.

    I learned a lot from watching Pat and his co-workers. They were constantly working on tight deadlines and big projects, but they always communicated with each other. I think Pat’s organizational skills and strong work ethic is why Ernst & Young named Pat Cavanaugh as the 2000 Entrepreneur of the Year.

    Eventually, these internships give you the skills to become a great player. After you become a great player, I think your next move is to go a weak team and make them great. Whether that means going to a struggling team to make them a contender or joining a company that is struggling in today’s market and making them a Fortune 500 company.

    I think it all depends on how you rate yourself. Are you a great player ready to lead a team or do you still need to watch others and see how they do things?

    It all comes down to how you view yourself. Great Blog post.

  2. Your post introduced some good arguments however I think personally I would rather be the worst player on a winning team because I feel like to be the worst among winners is always better than being the best among losers. I can be the best basketball player in Philadelphia and go to the NBA and be the worst player on my team. This doesn’t mean I am not good…it means I am positioned around so much greatness that I am no longer number one and with this comes an opportunity to be challenged to excel to even greater levels. If I am the best player on my team but they all are pretty bad players than that really doesn’t say much about myself.

    Think about this in the business world. Would you rather be surrounded by a team of colleagues who were by far more business minded, professional and career driven than you or would you rather be surrounded by people who really didn’t possess any of these characteristics so ultimately made you look good?

    Anyway just sharing my thoughts and by the way this was an awesome post!

  3. @James: I think the aspects you brought up of timing and how you rate yourself are very good points. For some people being a nobody on a winning team is completely satisfactory to them.

    A real life example…I was with my dad at a grocery store a few years back and this lady bagging groceries had a big smile on her face and said she had been there for 20 years. After I left I told my dad…If that was me I’d probably I’d feel like “What the hell am I doing with my life?” He told me each person has a different potential scale and a role. For some being a menial contributor at a winning organization is great. As long as their living up to their potential kudos to them.

    To me, I couldn’t just be a nobody on a winning team, eventually I would want to be a somebody on a winning team, even if I had to join a losing team to make that happen.

    @Martez: I would agree with you that it is often better to be a nobody on a winning team about 70% of the time. I strongly feel the more you hang around with winners, in business or sports, the more they’ll rub off on you. However there still comes a point where if your goal is to be the best person you can be (not to sound cliche’) you have to actually practice leading and one fertile environment to do so could be a losing team.

    thanks for the comments guys

  4. Being the worst player on a winning team still means that you win at the end of the day. You can’t say that about the latter.

    If we are actually talking about sports – being the best player may get you endorsements and deals, but your still a loser.

    The fact of the matter is, your back begins to hurt after carrying a team for so long.

    Putting it into perspective. Would you rather have a chain with 50 great links and one bad … or 50 bad links and one good ? Would you rather have 3 flat tires or 1 ? A centipede can’t walk with 99 broken legs regardless of how strong that 1 leg is.

    The only thing in people’s minds that makes them even consider this question whole heartedly is the fact that YOU are the good leg or the bad leg. Looking at a team the way that it should be looked at – it’s just a numbers game. How many good people are on the team ?

    Good post Dave.

  5. I like the metaphors that Anthony mentioned.

    I will have to agree with most that I would rather be the worst player on a winning team. The idea would be that you won’t always be the worst player, that you get better, you will get promotions.

    Winning the gold in the Special Olympics if you’re not special, can’t really satisfy a person’s goals and ambitions to succeed. Since we are talking about sports, you always want to play someone better than you in tennis and avoid playing weaker players because that is the only way to get better.

    Personally, I enjoy the feeling of facing a challenge, so I would enjoy being in a room of rocket scientists and challenging myself to understand and eventually contribute while some might feel intimidated.

  6. @Anthony great analogizes! Also a strong point about the reason that people consider this question. It really does depend on what your role is….Are you a coach (Investor), Team leader (CEO), Role player or bench player. I feel I could never be happy not contributing a significant amount to a sport or company that I’m a part of.

    @Carl I agree if you want to grow you have to be willing to step out of your comfort zone. It forces you to either sink or swim, and I feel we’re both the kind of people who are not going to sink.

    thanks for contributing to the conversation guys

  7. Fantastic question, if it were me, from an ego stand point, I would probably want to be the best player on a losing team. Still though being on the other side isn’t that bad either.

    Till then,


  8. Great article, I think you covered everything there. . . I would say freelancing is quite hard especially if you are not used to working on your own, can be quite hard to motivate yourself also. . . we all know what it is like to stare at the monitor.

  9. I am sure what team I would want to be on. I have been on both and had great experiences with both. While being on the winning team is fun I am sure I would want to be the worst player. My father used to coach me in soccer and was quite good at it. I was on a losing team and he was livid. He came to every game and coached even though he wasn’t our coach. We ended up bringing him on as coach and we won in the end. I don’t think there is any point in being the worst. If you are going to do something you should give it your all weather you win or lose. As long as you do that you are a winner.

  10. I found this article while searching for answers online because I feel I am the best player on a losing team. I started out this way and haven’t really been the worst player on a winning team yet. Maybe I should though.

    Great article! Thanks.

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