Have you enabled someone’s bad habits by caring too much?


My name is Bryan Wish and I’ve been an enabler my entire life. 

As a kid, I never told on “Shannon” for cheating off me in Spanish class. 

On my college intramural team, I never told ‘Eric” to stop finishing left-handed layups with his right hand.

Even now, I often find myself wanting to put other people’s short interests over what will be best for them in the long term. And you know what else? I don’t think I’m alone.

All jokes aside, growing up, I was probably enabled more than most and I established dependence on those closest. Hoping it would make me more independent, my father sent me on a three-week NOLS Outdoor trip that made me less reliant on others’ approval, and gave me the confidence to be more independent. 

I’ve been reflecting lately on the people who have managed me and the people I’ve managed in my own life. Striving to be a good person and surrounding myself with kind and driven people is a core personal philosophy central to my identity. When you try to be “too nice,” however, you often end up making the more comfortable decisions to avoid confrontation in the short term at the expense of better long-term solutions. 

When we never stand up for ourselves, people will continue with problematic behavior. In the end, letting this continue unchecked doesn’t empower them; it enables them to stay stuck in bad habits. 

Hold your teammates and personal relationships accountable for what they say they’re going to do. When they don’t, speak up and be direct when they don’t follow through. Having the wherewithal to stand up for what is right helps everyone involved in the bigger picture.

Understanding ourselves and where we personally need to grow better equips us to navigate the world independently. It’s equally important to help others do the same.

Featured Mission

Jeff Gothelf helps organizations build better products and executives build the cultures that build better products. He is the co-author of the award-winning book Lean UX and the Harvard Business Review Press book, Sense & Respond. Starting off as a software designer, Jeff now works as a coach, consultant and keynote speaker helping companies bridge the gaps between business agility, digital transformation, product management and human-centered design.

A man with an incredible journey, Jeff is a living, breathing example of the courage it takes to follow one’s passions. He left a cushy job and salary to help others find ways to stay Forever Employable, the title of his upcoming book. Jeff’s emphasis on lifelong learning and humility is among his standout characteristics and as a startup founder, I am learning a great deal from about a human-centered approach to scaling a business from his work. 

Because at the end of the day, scaling a business requires scaling your personal development at an equal or greater speed.

I highly suggest you connect with Jeff. Due in part to the unique, informed lens through which he perceives the world, he will become a valued addition to your network like he has been to mine.


Nate Andorsky has an exciting new crowdfunding campaign for his upcoming book launch, Product Behavior Fit!

Anyone who pre-orders a copy in the next 30 days gets access to these awesome perks:

  • A personally signed copy of his book upon release
  • A personal, handwritten thank-you note from Nate
  • Your name will appear in the acknowledgments section (“With special thanks to…”)
  • Early access to the book’s introduction 
  • The opportunity to provide feedback on cover designs and involvement in the selection process
  • A book topic/workshop seminar where Nate will share his experiences throughout the writing process

Nate is a great leader and person. Please help him out by spreading the good word!


Using Improvisation to Face Uncertainty

When things aren’t planned and scripted, it’s good to have tools in your toolbelt to navigate the situation. Here’s a TED Talk I recently watched on a top teacher in the improv space.

Work Rules, A New Book by Google Founder

When building a company, infrastructure, process and freedom become increasingly more important. At some point, every leader has to accept that you can’t control every detail anymore. With the right staff, you won’t need to. This book has been sitting on my shelf for years, and I’m picking it up very soon.

Film to Watch: Parasite

I tried something new this weekend and watched an indie film. By juxtaposing the elite and impoverished classes, it teaches a critical lesson. Turning a blind eye to something you know in your heart is morally wrong can lead to disaster. This impact is compounded when everyone else in a position of power does it, too. In the business world, this movie is what we would call an example of the Theranos story. Watch the trailer here!

I first heard this quote from my mom growing up, and it took me a long time to fully understand. Here’s my interpretation: It’s so much easier to see the good in people that sometimes you miss the “red flags.”  People that care too much can get blindsided by their “save the world mentality” in the search to help others. Having the relational awareness to understand how those “red flags” will make it easier to navigate down the road in any relationship, personal or professional.

In two weeks, I’ll be sharing an article on the self-discovery process, on how brand and personal discovery are very much of the same process. See you then!

The Pathfinder
Catherine Kushan

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