The flagship keynote
You Don’t Need a Five-Year Plan. You Need Five Options.
A keynote about building a life flexible enough to survive the plan falling apart.
Somewhere around age eighteen, people start asking where you will be in five years. They never really stop asking. The question sounds like planning. It is mostly pressure, and it quietly assumes the world will hold still long enough for the plan to work.
Chris makes a different argument. Direction matters enormously. Rigid five-year plans rarely survive contact with an actual life. What survives is options: the skills, relationships, reputation, experiences, and financial breathing room that mean when something you did not plan for happens, and it will, you have somewhere to go.
He makes that case as someone who spent twenty years building a very respectable plan, then kept saying yes to things that were nowhere on it. Law. Executive leadership. Businesses of his own. A film set. A microphone. He is not on stage to tell anyone he figured it out. He is there to argue that figuring it out was never the assignment.
The five options
The spine of the talk.
Five things worth building on purpose, each one illustrated with a story he can actually tell on himself.
Audience takeaways
What they leave with.
01
Less panic about the whole thing being figured out
The anxiety usually comes from a question that was never answerable. Naming that out loud changes the temperature of a room fast.
02
The difference between direction and a rigid plan
One is a compass and the other is a cage. Most people are handed the cage and told it is ambition.
03
A practical way to create opportunities on purpose
Options are not luck. They are built, usually in small and unglamorous increments, and the building can start this week.
04
Permission to try, miss, adjust, and go again
Chris talks about his own bad calls specifically, because a speaker with a flawless record is not useful to anybody.
05
A career seen as a stack of options, not a single ladder
Ladders have one direction and somebody else owns them. A stack of options is yours.
06
Proof that ambition and humor can coexist
Serious about the work, unserious about yourself. He is a lawyer everyone calls Shmiddy. The whole brand is the evidence.
Who it is for
Written for students. Sharp enough for executives.
The talk was built for people early in a career, but the argument does not soften for an older room. Anyone who has ever been asked to predict their own future recognizes the problem immediately.
- Incoming students and orientation
- Student leadership and honors
- Career services and career readiness
- Graduating seniors
- Entrepreneurship and innovation centers
- Greek life and campus programming
- Young professional organizations
- Associations and corporate audiences
Why his delivery is different
Stories, not slides.
Operator credibility
Twenty-plus years practicing law, Chief Legal Officer of a health and wellness company with more than $3 billion in lifetime sales, and businesses of his own. The stories are first-hand.
Humor with a job to do
He is a humorist. He writes his own material, and the laughs are timed and load-bearing rather than sprinkled on afterwards.
Specifics over slogans
The night-school semester. The deal that went sideways. The audition he had no business being at. Bullet points do not survive a week. Stories do.
Shaped to your room
He will ask who is in the seats and what the event is for, then adjust the examples accordingly. Same argument, different evidence.
Formats
- Keynote45 to 60 minutes, plus Q&A
- Short-form keynote20 to 30 minutes for a packed agenda
- Workshop75 to 90 minutes, interactive, smaller room
- Fireside or moderated Q&A30 to 45 minutes
- VirtualLive, not pre-recorded
Put this talk in front of your room.
Send the date, the audience, and what you want people thinking on the way out.