Failing Forward

February 23, 20222 min read

source: dilbert.com

Sharing two lessons I found interesting from a talk by Tim Ferriss.

1 - How to Win Even as I Fail

Whlile we typically view "failing upwards" as something negative — someone earning undue success, having their incompetency unfairly rewarded — failure doesn't necessarily have to set us backwards.

When choosing a project to dedicate our time and efforts into, we need to be deliberate and consider beyond what we can gain when things go well. And this means looking at what skill set, domain knowledge, and relationship we will develop that can transcend and persist even after the project tanks.

For instance, advising and investing in a startup that — even if it doesn't work out — would help you develop trusted relationship with the founders and plant the seeds for future collaboration.

Or working on a new podcast idea that would equip you with content creation and marketing skills that is transferable to your next project even if the podcast doesn't take off.

When we are deliberate about the projects we invest our time or money in, every failed project will bring forward a positive snowball effect, usually in the form of relationships and transferable skills, that will give you 10x or 100x returns of investment later.

Even if you are not working on so-called "projects", this concept can also apply to your career. Work on companies or internal teams / opportunities that, even if things don't work out, will provide you with high-leverage outcome in term of relationship or skill set.

Looking back the past 2.5 years, I have worked on three different projects:

  • In BorrowMind, I learned product distribution and marketing, fund raising, and the importance of founder-domain fit.

  • Osoji is a valuable arena for me to dive deep into the technical and business aspects of building a new consumer application, and how to iterate and position a greenfield product with feedbacks from users.
  • In advising a NFT project, I learned more about the crypto space and the quirks of NFT marketing and community building.

While the positive snowball effect Ferriss suggests is not always immediate and apparent, I am hopeful my investment in these projects will reap multifold returns as I carry forward my learnings and relationships to the future.

2 - Generalist vs Specialist

How do we compete and stand out in our career? Is it better to be versatile and capable of drawing from a broad and diverse set of knowledge? Or to have a narrow but deep set of skills?

Scott Adams, the creator of Dilbert comic strip, recommends combining a handful of skills that are rarely combined.

In most fields, financial returns and successes are typically disproportionately skewed towards the top. For example, if you specialise in basketball, you need to be top 0.0001% to do well financially. If you are a scientist, most of the honors and recognitions go towards the top few Nobel winners. So mathematically, if you specialise in just one thing, it is a long shot to get to success.

On the other hand, if you combine two skills that are valuable and rare together — e.g. computer science and law degree, or medicine and data science, or finance and public speaking — you automatically stand out and get a competitive advantage in your field.

This means becoming a specialized generalist, mastering 2-3 skills are potent and effective to combine but rare as a package, instead of dabbling into 10 different skills and being a master of none.

If you are a specialist, you can think about what are some add-on skill set or domain knowledge that would give you a multiplier lever and stand out from your competition.

Public speaking, writing, and negotiation skills, according to Tim Ferriss, are the three natural boosters to any career. As an example, Warren Buffett believes his best investment was in a $100 Dale Carnegie speaking course. Good communication and public speaking skill, being able to share information to shareholders and CEOs effectively, has made him a much better investment manager.

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