I recently read a short essay called “A Streetcar Named Success” by Tennessee Williams, the renowned mid-twentieth century American playwright who wrote A Street Car Named Desire and The Glass Menagerie. The essay talks about how life became a bit disjointed after he became “successful” and started living a life of luxury — living in a hotel and getting room service all the time. He started hanging out with different people, found it difficult to be creative, and just felt more detached from the world. Continue reading

When approaching a problem or a challenge there are two main approaches you can take: being strategic and being opportunistic.

Being strategic means thinking through all sides of the problem. Looking at what people have tried, what’s worked, what hasn’t. Considering the context of the problem and how this context evolves over time. Mapping out a plan, executing on it and taking the time to measure your progress against metrics you’ve established. Strategic is Billy Beane and the Oakland A’s.

Being opportunistic means taking things as they come. Looking at what makes sense right here, right now. Jumping right into the thick of things and figuring it out as you go along. Exploring interesting connections, poking your nose into strange places and smashing stuff together to see what happens, always angling toward a particular, but vaguely defined, direction. Opportunistic is the story of Todd, Ben Folds Five and Improv Everywhere.

Each approach has it’s trade-offs:

  • Thoroughness vs Speed.
  • Protected downside vs Unlimited upside
  • Steady progress vs Rollercoaster ride.

There’s no right or wrong approach. But you ought to recognize that there’s a difference and try to make the decision a deliberate one.

How do YOU approach your problems? Are you strategic or opportunistic? Tell me in the comments!

I’ve been mulling two semi-related work habits/beliefs that I think really contribute to individual & team success. I see them in a lot of people I admire and to be honest, they are habits that I’m glad I’ve naturally adopted.

1) There is Always More You Can Do

A few months ago, my coworker/direct report said to me “Well, I finished my all my stuff for today so I’m taking off early.” She does a great job, but her attitude didn’t rub me the right way. The next day I told her:

“If you feel pretty ahead on your work and you’ve been putting in long hours, sure, an early day is fine. But don’t make the mistake of thinking you’re actually DONE with all your work.”

You are NEVER done.

There is always more you can do – more industry research to do, more analysis to perform on the metrics you track, more phone calls could be made to a potential clients / partners, more practice on the presentation you have next week, more emails to write (perhaps to a coworker saying “thanks for your help on project X”), hell, more icon cleaning on your desktop to perform.

People who are sucessful get ahead because they recognize that the number value-adding activities are endless and are always doing much more than is strictly required, because you don’t achieve great thing by doing just enough.

2) Take Initiative / Responsibility for Improving Everything

If you don’t like some aspect of your firm or your work life – salespeople aren’t closing, the payroll process sucks, your boss never responds your emails, the press releases the PR team sends out are super-bland – don’t just blame someone or throw your hands up in frustration.

Do something about it.

Build relationships with the various departments and stakeholders so they trust & respect you. Learn about what they do and study industry best practices. Ask the HR team if they’d like feedback from the staff, have a meaningful conversation with your boss, forward your PR team a press release you like, talk to customers about what closed the deal for them and send the insights to the sales team. I hate it when people say “that’s not my responsibility” because it is a sign of apathy and helplessness that is not productive.

I’m not advocating shirking your own job responsibilities, just that you ought to  proactively address other areas if you feel you can help the firm improve its performance.

These ideas may be a little off putting to some people and it’s possible that they can backfire (burn out & angry coworkers come to mind) but I do believe that people who adopt these mindsets will ultimately add more value to their organizations and be more successful.

Read a great post on how a salesman turned around a client who HATED his company into the deal that changed his life. (He wrote 2 handwritten notes a week for 3 months, then worked 24 hrs straight to deliver when she gave him a job). But you got to read it for yourself.

Here is what he learned.

  • Stay commited.
  • Focus on Changing the Game.
  • Be Sincere.
  • Be Different.
  • Risk being laughed at.
  • Risk FAILURE every day.
  • Write handwritten notes.
  • And, most of all positive karma — or leave what you are doing.
  • Develop Entreprenurial Improvisation.