Financial stability and risks

Over the past several months, I’ve realized how important financial security is for individuals and organizations.

When you have financial security, you have more room to breathe and take risks. Things aren’t as urgent. Your survival as an individual and a organization aren’t on the line.

For companies, this translates into a willingness to be more experimental and exploratory with their initiatives. It deprioritizes near term financial gains and optimizes for learning that could yield more in the future.

For individuals, the same dynamics apply. If you have financial security, this means that you have more capacity to invest in the future. These investments can be in the form of education or exploring your interests. Again, taking some level of risk now, for a bigger gain in the future.

Without financial stability, individuals and organizations have a zero sum mindset. Short term gains are urgent and needed to survive. A ticking clock when you don’t have enough money is very stressful. This creates the conditions for our worst parts to surface. Survival is a stress test for your values.

This can create a negative feedback loop. Where short term behavior for financial security means we don’t have a way to dig ourselves out of a financial hole.

When you’re prospering, it’s easy to take more risks to reap more rewards. When you’re suffering, it can feel nearly impossible to escape the cycle.

In the context of our world today, if you aren’t in the suffering cycle, then it means that there’s room to invest and support others.

Better Meetings and Decisions Workshop

One of the most important skillsets I have learned in the past couple of years was to listen and facilitate conversations. These two skills are now foundational to how I work toward better meetings and decisions.

These aren’t the skillsets that are talked about much for product designers, but it’s critical in order to do great work. I was excited to see John Maeda include it in his list of 10 near-term skills to help designers grow for his 2018 Design in Tech Report.

Learning to listen and facilitate conversations has helped me any time I’m working with someone to evaluate and make decisions.

As product designers, this encompasses a lot of situations at work

  • How does your team align on the problems to tackle?
  • How does your team provide feedback on your work?
  • How does your team decide when something is done?
  • What is the scope of work your team is planning to design, build, and ship?

On a meta-level

  • How does your team make decisions?
  • How does your team communicate agreements or disagreements?

Learning to listen and facilitate conversations has changed the way I approach all of these questions. The side effects of ineffective decision making means that team members could eventually give up disagreeing and avoid fully committing to the decisions. There is also the cost of taking too much time and energy to align on a decision.

Being a good listener and facilitator makes these conversations more productive. As the team gets better, it also means that you’re making decisions faster and the decisions are more aligned. Listening and facilitating are prerequisite skills for collaboration and leadership in any group setting.

If you’re a designer or PM interested in improving your listening and facilitation skills, I’d love to share what I have learned with you. There aren’t a lot of resources out there geared toward designers and product managers. So I’m going to start small group workshops to teach these skills. Let me know if you’d like to learn more about the workshops by signing up here. I’ll keep you updated when the first one is scheduled.

Education Inspiration

I was listening to a recent TED Radio Hour episode on Rethinking School. The four chapters of the episode inspired some observations:

How do we get kids hooked to science? Start with stories, and use the right level of details. It’s okay to not be 100% accurate and it’s okay to leave out details, because it’s more important to get someone to understand the concepts before they can go deep on the details. Your approach to educate a 13 years-old should be different from talking to a PhD researcher.

What can we learn from comparing education systems around the wold? There are places where teaching is a coveted and prestegious profession. Students are more likely to succeed if they have a growth mentality toward their learning, rather than one where success is only possible for those gifted at specific subjects. With so much information available, focus on how to creatively use concepts rather than regurgitating them.

Sal Khan’s approach to a physical school: Focus on progression and advancement, mix students from different ages rather than separating them by grade levels.

Empowering students in poverty Linda Cliatt-Wayman uses several slogans to get her message across to students and teachers.

  • “So what, now what” rhetorically encourages them to take ownership of their future regardless of their unfair and unfortunate circumstances.
  • She also reminds them her unconditional love toward them and of her belief in their ability to succeed. Every day on the PA system, “If no one told you today that they love you. Remember that I do, and I always will.”

That last part reminds me of the Radical Candor framework. The person you are trying to help won’t be receptive until they see that you actually care about them.

It takes a lot of work to create a safe learning environment, and I’ve been fortunate enough to have experienced it at schools, at home, and at work. Four years ago, I posed a similar question to consider what our learning environments could look like after we graduate from school.

On Should

I’m not sure the origin of this thought, what inspired it, or where I was when it happened, but here it is.

The word should is loaded. It carries the weight of implied expectation that can be detrimental to relationships. When we say something or someone should exist or be some way, we are communicating our expectations on how the world should be, but isn’t.

Should is the bridge between ideal and real. It is the gap between potential and not yet or never. I should; you should; we should; they should. Embedded in that word is an expectation that imposes my view on others. I am asserting a desired or expected state of the world, and I communicating that the world has failed to meet those expectations.

  • They should… is projection.
  • They should have… is judgement.
  • I should have… is regret that comes from hindsight.
  • I should… is external expectation that I don’t believe in or want yet.

The next time you hear should, figure out the embedded expectation and where it stems from.

Recent Urban Planning Books

I’ve been reading about urban planning recently.

I’m drawn to them as a designer because people are at the center of them, and there are a multitude of complex systems that influence each other.

Our quality of life is affected by how our cities are designed. Building zoning and transportation options affect where we work, live, and commute. It affects how we relate to our neighborhood and our neighbors; what we perceive to be desired and undesired parts of the city and transportation options.

Recent Urban Planning Books

  • Happy Cities: Explores the tension between our need to have a lot of private space and how that conflicts with our preference to be close to the attractions and conveniences of a city.
  • Street Fight: A first person view of Janette Sadik-Khan’s work in changing the street layouts of NYC. If you live in NYC, you will look at a crosswalk through a new lens. There are also glimpses into the cost of maintaining infrastructure and how bike sharing was introduced. Janette explains the methods her team used to gradually test and introduce changes to the streets.
  • Bowling Alone: A dense view of the changing attitudes toward civic participation and how it affects our communities. Robert Putnam dissects a range of possible causes and explains how they are interconnected.

Cities are messy. They are a series of overlapping snapshots of our culture. It’s container for all the things we value, aspire to, and are willing to tolerate.