See “Blackstone’s Byron Wien Discusses Lessons Learned in His First 80 Years” for the full list of twenty items. The numbering here is preserved from the original list.

2.  Network intensely.  Luck plays a big role in life and there is no better way to increase your luck than by knowing as many people as possible.  Nurture your network by sending articles, books and emails to people to show you’re thinking about them.  Organize discussion groups to bring your thoughtful friends together.

There are several ideas in this item that are worth unpacking. We also need better applications to support this approach, not to substitute for conversation but for memory.

  • Curating a stream of information requires that you keep careful track of the needs and objectives of the folks you are reaching out to. A short e-mail with one or two sentences of comment and an obscure link sent to an individual or small group is more effective than re-broadcasting a popular article to a large list.
  • I find that organizing a dinner for two to five other folks every two to four months is often an effective group size and interval to allow for a lively and thought provoking discussion.
  • If you find yourself sending the same article and analysis to multiple different people it may also be worth a blog post.

4.  Read all the time.  Don’t just do it because you’re curious about something, read actively.  Have a point of view before you start a book or article and see if what you think is confirmed or refuted by the author.  If you do that, you will read faster and comprehend more.

I think short topical or practical articles are useful but it’s as helpful to read as much fiction, biography, and historical analysis to reset your mind from running in the same grooves.

5.  Get enough sleep.

Historically I have honored this advice more in the breach but believe that it’s worth keeping track of, along with:

  • Bedtime: the decision to get enough sleep typically means you have to go to bed early enough.
  • Wake-up time : if you are having trouble getting out of bed for more than a two or three days in a row you need to make changes in how you are spending your time and energy.
  • Exercise: here I think workout buddies or small group activities can do a lot to help maintain discipline in this area.
  • Weight and diet: any significant weight (say 5 pounds outside of your normal range) has to be managed immediately, not once the project is done or the product ships or your startup gets acquired.
  • Meditation / prayer, / a regular time set aside where you can relax and reflect

12.  When someone extends a kindness to you write them a handwritten note, not an e-mail.  Handwritten notes make an impact and are not quickly forgotten.

If your handwriting is terrible then print. The act of counting your blessings and taking the time to thank folks in writing, in person, or in public is never a wasted effort.

13.  At the beginning of every year think of ways you can do your job better than you have ever done it before.  Write them down and look at what you have set out for yourself when the year is over.

At the end of every project or significant deliver you should solicit suggestions from everyone involved: co-workers, partners, and customers. It’s as important to understand what worked while and what was valued as what needs improvement so that in addressing one problem you don’t break something else. Explicit checklists can also be helpful for raising your game.

14.  The hard way is always the right way. Never take shortcuts.

I interpret shortcuts to mean actions that cross an ethical boundary or that you would not want friends, co-workers, partners, customers, or family to know that you did. Finding smarter ways of doing things or skipping the truly unnecessary is always a good idea, but if you are contemplating something and conclude “what they don’t know won’t hurt them” it’s worth re-thinking.

15.  Don’t try to be better than your competitors, try to be different.  There is always going to be someone smarter than you, but there may not be someone who is more imaginative.

This is very hard. Breaking your own trail in many ways feels riskier than coming in second (or seventh or 199th) but I think it’s essential for bootstrappers. It’s also OK to tie or even not be as good in areas where your customers–versus their customers–care less then in the area or areas you are innovating.