I chat with technology leaders from time to time and we discuss how technology is rapidly evolving. In ten years some types of problems might not be problems anymore or are solved as easily as importing a package. I want to keep a running list of topics that are hard. I think it is beneficial for a long term career to focus on solving the hard problems. It seems like on-going cultural change is an ever-lasting challenge. I would love to hear from others what they consider as being hard to solve.


  • Building new systems
  • Adding new tools and systems
  • Adding features
  • Building synchronous systems


  • Building compute platforms
  • Validating new products and ideas quickly and cheaply


  • Scaling software cheaply
  • Software that adapts quickly as the world changes due to laws, competition, etc
  • Data Locality
  • Moving from Synchronous systems to asynchronous systems
  • True Root cause analysis
  • Maintaining software systems
  • Training software developers on new tools and systems
  • Sunsetting old systems, APIs
  • Deleting features and removing functionality
  • Validating that a specific feature is needed or will be used
  • Consciously designing teams and reorganizing teams as needed
  • Leadership
  • Coaching
  • API Management in the Enterprise
  • Obtaining and maintaining organizational alignment and focus
  • Cross skill training of different specialties Software Engineer, Data Engineer, Infrastructure Engineer
  • Institutional Inner Code Sourcing
  • Communicating
  • Teaching
  • Domain-Driven Design
  • Standardized data models and contracts across business systems
  • Enabling teams to be prompted to behave a certain way
  • Time and the ability to train staff for situations
  • Database observability
  • Visualization of systems
  • Leaders that create leaders
  • CRUD automation for less than $1
  • Rewriting old systems
  • Organizational Change
  • Entrepreneurship
  • The 10 to the 20-year unclear value proposition
  • Hard-won business knowledge
  • Hard-won software design knowledge
  • Solving one problem and keeping it solved
Contact me

Let’s Start a Project