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What I Wish I Knew at 21

What I Wish I Knew at 21

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Having recently suffered a personal loss, I’ve been doing a lot of soul searching and along the way realized a number of things I wish I had known when I was 21.  I wouldn’t ordinarily post something so personal but as I started to think about it, there are some hopefully useful tips in there which might help other aspiring PMs or Microsofties-in-training. 

Failure is key to success

You will fail way more often than you succeed and too often people focus on the ratio but ignore the lessons that failure provide.  My greatest successes have always followed a failure, sometimes catastrophic failures. Don’t use failure as an excuse to stop or hesitate.

Invest in yourself

Always give yourself time to grow, learn new things, meet new people, and expand your comfort zone.  Invest time, money, and energy in yourself because it always has the best rate of return. For those who have a hard time with this type of selfish activity, realize that your ability to help others is limited by how you yourself grow.  I find that this is especially hard as a parent but even more critical (applies to any “leadership” role)

Know your weaknesses

Self-evident.  What may not be so obvious is that this is an ongoing exercise.  You never stop learning new things about yourself, at least as long as you never stop looking.

Plan if you need to, but don’t stop executing

Plans, like slide ware, look good on paper but never beat actual results.  Not to say that planning is not important, especially as a PM, but don’t get lost in the plan or be afraid to improvise.

Fear or discomfort are signals to try something new

Listen to what your heart and mind are saying …. but don’t always follow them.  You will not grow if everything you do is comfortable.

Everyone is smarter than you

I mean that in a literal sense – the sum of the experience, skills, and knowledge of the people surrounding you will almost always surpass what you individually can contribute.  Don’t hesitate to tap into that pool of knowledge.  Ask questions.  Learn.

Be skeptical and trust yourself

Don’t accept everything at face value, especially if it is “common knowledge”.  Innovation comes from questioning the norm.  Genius is often proving conventional wisdom wrong.  Your gut instincts are usually pretty good and worth trusting if they are telling you something is wrong. 

Do something different every day

Make a change in some part of your routine on a daily basis.  Habits become ruts and your presumptions become blind spots. 

Play and work

No one successful is boring. They all have passions outside of work as well as being passionate about their work.  Your external perspectives are what make you unique and give you an ability to solve problems in your own special way.  Don’t let work prevent you from playing.

Pick what defines you very carefully

If that is your job, make sure your job is your passion – something you truly love.  If it’s not your job, that’s OK too, but know that and make an intentional decision.  Don’t settle.  I once told a PM in my team that you shouldn’t work at Microsoft unless you are working on something really big – the next cool thing that will change the world. Do not come to Microsoft unless you intend to change the world.  Do not stay at Microsoft unless you think you are changing the world.  Do not settle.

The most important impact you will have will be on someone else

It’s all about people.  Never forget that. Easy to lose site of that because we work on software/things.  The end goal is always about people.  The impact you have is about how you touch those people you work with, live with, and work for.

You have only one chance to live your life

There is nothing worse than regretting the action you didn’t take, the words you didn’t say, or the opportunity you passed up.  When you come to that decision point, ask yourself whether or not you will look back and regret not saying Yes.

  • Thanks, I read every single sentence. Good stuff you got.

  • Sean, this is up there with my all time fave blog posts - great stuff!

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