24 Things I Know Now That I Wish I Knew Then

I really liked Rae Hoffman’s post from last month, Entrepreneurial Lessons: 48 Things I Know Now That I Wish I Knew Then. And, while I don’t agree with everything on her list (at least as it applies to the experiences I’ve had), I felt compelled to take up the format she’d presented and do something similar.

(via waltërcin on Flickr)

Unfortunately, I don’t have 48 lessons to share, but I can pitch in half that – 24.

  1. Don’t conflate revenue with success, especially not long term. Many of the best things we’ve done have cost or lost money in the short run, but built a better brand over the years because of it.
  2. Setting goals and creating roadmaps is a good exercise  Limiting your creativity or options because you’ve set them in stone mentally and emotionally is dangerous.
  3. There’s a philosophy I’ve often seen espoused which theorizes that past success is the only indicator of future performance. I reject this entirely, and have loads of evidence to back up the loser-turned-winner narrative.
  4. A friend in college used to regularly tell me to “Never date the pretty girl who knows she’s pretty.” Extrapolated out to the professional world, I’ve found this to be excellent advice. Those who think very highly of themselves tend to make for poor employees, partners, service providers, friends, spouses, etc.
  5. Money can’t buy you love, but it can buy you time. Spending money to buy time has some of the highest ROI I’ve encountered.
  6. Being genuinely interested in other people is very powerful and highly enjoyable. I can’t recommend it enough.
  7. Aligning yourself with people who share your values and your prioritization of those values far outweighs aligning yourself with people who share your vision for a particular product, roadmap, or financial goal.
  8. No one succeeds on their own. Avoid those who believe they have (or will).
  9. Failing is the best way to learn. Being scared to fail directly correlates with being scared to learn.
  10. Better marketing often trumps a better product. Invest in both.
  11. People are irrational, but in surprisingly predictable ways. Knowing how makes you far less susceptible to the unpleasant emotions that often accompany the discovery of such irrationality.
  12. Don’t bother having enemies. I like to believe that people who don’t like me are simply folks I haven’t spent enough time with yet (though sadly, I likely won’t ever have enough time for some of them).
  13. Spending time with people who have things really, really rough can help remind you about the relative importance of that person who was mean to you on Twitter.
  14. The web is a vast and wonderful place, and exploring it with an open mind that’s desperate for inspiration can lead to amazing things.
  15. If you ever catch yourself refreshing a comment stream or message board post over and over waiting to argue – they’ve already won.” – I’m stealing this one from Rae, but only because I so vehemently agree, and I’ve lost so many times to this rule without realizing it.
  16. Generally avoid comments on Yahoo! News, Youtube, and anything political, despite what #14 says, as these will make you fear for the human race.
  17. Stereotyping becomes mathematically more dangerous the more people you meet.
  18. The rules of bullying don’t change much from when you’re a kid. Those who bully are generally more insecure than you, and usually back off if they’re either A) ignored or B) faced by a bigger bully. There is one rule change – A is much easier, wiser, and more legal than B as you get older.
  19.  Pretend that all your legally enforceable documents (which you should take care of) will never be practical or worthwhile to enforce. This will push you to work with people you believe will always be trustworthy and ethical to the spirit of these agreements.
  20. Nothing worth having comes easy. Relationships (of all kinds) take work. Customers take work. Building a team takes work. If it’s easy, it’s often not worth having and almost never a competitive advantage.
  21. Investing where others do not is usually the best way to succeed. Investing where everyone else already does is usually the best way to be mediocre.
  22. If you advise others in their business, formally or informally, whether on the team, the board, or neither, you do a disservice when you don’t question assumptions and demand evidence. Critical feedback, hard questions, and tough conversations make us better at our work.
    Caveat #1: Never do this from a place of hostility or hidden motivation. The best disagreements and discussions are between those who have respect, admiration, and love for one another at the core of the relationship (exempli gratia).Caveat #2: This may work terribly in your purely personal relationships. Your wife/friend/brother (usually) doesn’t need you criticizing their decisions and asking them hard questions. They need you backing them up 100%. I think this is why family and business often don’t mix well.
  23. Most people massively overvalue secrecy and massively undervalue transparency. This makes sharing openly even more unexpected, remarkable, and powerful.
  24. People don’t buy what you do, they buy why you do it. This is why I won’t buy anything from Apple, why Kickstarter works, why Harley Davidson continued to have success despite terrible quality in the ’70’s and ’80’s, and why many startups have a hard time marketing themselves.
I’d love if more folks picked up this format and shared some of their own lessons. If you do, feel free to post a link in the comments below.