Stan Rosenberg: Applying Perspective

Picture of Stan Rosenberg

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Stan Rosenberg, Founder of Trip of a Lifetime, shares ways to apply perspectives gained from work and travel to your After Hour Project.

Since its inception in 2009, Trip of a Lifetime has provided summer travel scholarships to over 200 students, and has been recognized for its efforts by the Wall Street Journal, NYC Department of Education, and Rotary Club International.

We cover the story behind Trip of a Lifetime from Stan’s transformative travel experience in high school to him building the organization, continuing throughout college and post-graduation plus much more on professional development.

Episode Highlights

Don’t be afraid to ask

If you have a “simple hook” and believe you have value to offer, don’t be afraid to reach out to others and follow up.

Stan got in touch with his first travel partner organization by writing them a cold letter.

Creating a personal “Board of Advisors”

It’s really hard to do something alone. It’s much easier when you have the help of others, ideally from varying backgrounds who can give advice from different perspectives.

Stan and his team worked with former teachers, professors, friends, and donors to advance their organization.

On Professional Development

  • Optionality – starting out, it’s important to pursue opportunities with option value, letting you build a wide variety of skills and opening doors to future opportunities
  • Range – a book making the case for generalists succeeding in a specialized world, stating that one important skill is in connecting the dots across multiple disciplines
  • The “T” Framework – a career framework of having a specialized skillset in one area while still having broad knowledge of a variety of fields
  • Balance – focusing on high-impact activities and delegating the rest
  • Creating your niche – oftentimes, you can combine two disciplines to create something completely new and be the best in your field

Stan’s advice for those looking to work on a passion project on the side

  1. Start out small to test what you want to work on and gradually build it – eventually, there will be a snowball effect towards scale
  2. Have conversations with lots of people to gain perspective and knowledge
  3. Leave room for opportunities: maintain relationships with others and be helpful – you never know what doors may open

More about Stan

You can find Stan on Twitter at @stanrosenberg

Trip of a Lifetime website:

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