Getting Going
Your early days are not about landing the perfect job – it’s about building a trajectory.
In other words, unleashing opportunities for more upside – and more lifetime value – throughout your career.
Early roles should ask more of you than you think you’re ready for. They’ll teach you how to show up when the work isn’t glamorous, how to grow into responsibilities you haven’t held before, and how to build the foundational skills that will serve you for a lifetime.
Here’s our tactical advice, honest reflections, and tools to help you navigate your first few years: how to build a resume that opens doors, how to get into rooms where real work happens, how to develop the habits and capabilities that make you indispensable, and how to take the risks most likely to uncap potential two, five, 20 years down the road.
It’s not about shortcuts – it’s about momentum. Let’s get moving.
Hitting Singles vs. Home Runs
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Early in your career there’s huge pressure to “swing for the fences.” But inside a small business team, trust is earned through the steady drip of unglamorous, done-right-the-first-time tasks. Sarah George-Waterfield sits down with Holly Grajera, Danny Gray, and Tim Hanson to unpack how doing the small stuff (from color-coded spreadsheets and back-office macros to simply replying to emails fast) can unlock big opportunities over time. Learn why consistent singles, not occasional home runs, win the long game.
Listen for …
Soft-skill “singles” that compound into career-defining credibility
How to quietly fix things, even without permission
The six traits that widen your opportunity set
A practical rebuttal to the “do only what you’re paid for” trend
Why potential energy from steady effort eventually explodes into kinetic wins
Timestamps
0:00 Intro: – Small Ball Beats Big Swings
1:07 Holly Grajera – Hitting Singles: typo-free emails, bagel orders, “How to Say Things Nicely” cheat sheet, living deal-tracker spreadsheet, Instagram intel
9:02 Danny Gray – Automating the Annoying: Taking ownership of the irritating tasks and building credibility with the team
10:24 Tim Hanson – Potential → Kinetic: Showing up with effort, building network width, and why you don’t need to “win” every day 15:05 Closing Takeaways – Do the unglamorous stuff wellResources & Links
Book: Getting Things Done by David Allen
Tim’s Newsletter: Unqualified Opinions
The Orbit Talent Network, Personality Test, & Roles: The Orbit
Sponge Learning
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Growth rarely happens in isolation. In this episode Sarah George-Waterfield digs into “sponge learning” – the art of asking the questions you’re afraid to ask, parking yourself in the right rooms, and wringing every drop of insight from the people around you. Danny Gray, Joe Swanegan, Holly Grajera, and Tim Hanson share how curiosity, reps, and informal mentorship helped them leap industries, level up skills, and earn trust inside a small business team.
Listen For …
Why “dumb” questions aren’t dumb – and the costs of not asking them
A step-by-step “rep game” for mastering a brand-new field
Practical ways to reverse-engineer great calls, meetings, and emails
How to find mentors without the awkward “Will you be my mentor?” email
Using curiosity as a magnet for senior allies who want to teach you
Timestamps
0:00 Intro — What Is “Sponge Learning”?
1:07 Danny Gray — Asking the “dumb” questions before they become expensive mistakes
3:37 Joe Swanegan — The Rep Game: consuming info, saying it aloud, testing it, getting humbled, repeating
4:56 Holly Grajera — Reverse-engineering great work: context-call note-taking, informal mentors, being physically present
10:19 Tim Hanson — Curiosity as a mentor magnet, “return on effort,” and why experts love to share
17:37 Closing Takeaways — Chase curiosity, use other people’s brains, always follow throughResources & Links
Book:Getting Things Done by David Allen
Tim’s Newsletter:Unqualified Opinions
The Orbit Talent Network, Personality Test, & Roles:The Orbit
"Safe doesn’t, hasn’t, and won’t generate outsized returns."
“You can't have an outsized outcome if you go for the predictable path.”
— From Emily Holdman in “How to Buy Great Businesses,” The Fort
“You should only bet on things that have the optionality to go really, really well if they work.”
— From Tim Hanson’s “There Is No Medium Risk”
In other words, no career move is truly “safe” — staying put, starting over, or jumping industries all come with risks. The key is to choose risk intentionally, not avoid it entirely. Safe bets can have hidden costs (like stagnation or burnout), just as bold ones can carry real upside.