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# The Power of Philosophy Fit in Business and Life
- URL: https://robweidner.com/the-power-of-philosophy-fit-in-business-and-life/
- Published: 2025-02-11T16:30:41.000Z
- Updated: 2025-02-11T19:38:56.000Z
- Author: Rob Weidner, PMP

> *“The key is to keep company only with people who uplift you, whose presence calls forth your best.” –* [*Epictetus*](https://en.wikipedia.org/wiki/Epictetus?ref=robweidner.com)

In a world obsessed with [**product-market fit**](https://en.wikipedia.org/wiki/Product/market%5Ffit?ref=robweidner.com), [**go-to-market strategies**](https://www.gartner.com/en/insights/sales/insights/what-is-go-to-market-strategy?ref=robweidner.com), and [**physical fitness**](https://www.cdc.gov/physicalactivity/index.html?ref=robweidner.com), we often overlook something more fundamental: **philosophical alignment**. This deeper *philosophy fit* shapes not just our work but also our choice of [partners](https://hbr.org/2020/05/how-to-choose-the-right-business-partner?ref=robweidner.com), [mentors](https://tribeofmentors.com/?ref=robweidner.com), and [tools](https://zapier.com/blog/best-productivity-apps/?ref=robweidner.com)—ultimately driving our vision forward.

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## [37signals](https://37signals.com/?ref=robweidner.com) and the Power of Transparency

Few exemplify **philosophy fit** better than [**David Heinemeier Hansson**](https://dhh.dk/?ref=robweidner.com) ([DHH](https://twitter.com/dhh?ref=robweidner.com)) and [**Jason Fried**](https://world.hey.com/jason?ref=robweidner.com) of [**37signals**](https://37signals.com/?ref=robweidner.com). Their writing is refreshingly human—free of [AI-generated](https://openai.com/chatgpt/?ref=robweidner.com) LinkedIn clichés, emojis, and buzzwords. Beyond that, they create tools that challenge conventional thinking. Their product, [**Basecamp**](https://basecamp.com/?ref=robweidner.com), has become my go-to project management solution, both personally and professionally.

Over the years, I’ve experimented with nearly every project management platform:

- [**Custom-built**](https://www.airtable.com/?ref=robweidner.com) Airtable solutions
- [**Structured**](https://asana.com/?ref=robweidner.com) options like Asana
- [**Heavyweights**](https://www.atlassian.com/software/jira?ref=robweidner.com) like Jira

The modern **build-vs.-buy** dilemma is overwhelming. Businesses now juggle a dozen tools to function—far removed from the days of picking up [three CDs](https://www.microsoft.com/en-us/microsoft-365?ref=robweidner.com) (Windows, Microsoft Office, and QuickBooks) and launching an operation overnight.

### Why [Basecamp](https://basecamp.com/?ref=robweidner.com) Stands Out

Basecamp thrives due to its **perfect balance of flexibility and simplicity**. It adapts to businesses rather than forcing businesses to adapt to it. Its **unconventional** [**API**](https://github.com/basecamp/bc3-api?ref=robweidner.com) and [**affordable pricing**](https://basecamp.com/pricing?ref=robweidner.com) make it even more appealing. The revival of a [**free tier**](https://basecamp.com/solo?ref=robweidner.com) for single-project teams is a nod to the early days of entrepreneurship—when all you needed was an idea and a bit of software.

What really resonates, though, is their **commitment to transparency**. The [customer stories on their site](https://basecamp.com/paths?ref=robweidner.com) don’t just highlight features—they showcase real people who believe in the **product** and its **philosophy**. That same transparency has inspired me to write more openly and embrace vulnerability in my own work.

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## Why “AutomateY”? The Power of *Why*

You might wonder why I focus so much on **philosophy fit** in this newsletter. I once considered naming it **“AutomateY”** (or **“Automayte”**) to emphasize the importance of [**why**](https://simonsinek.com/find-your-why/?ref=robweidner.com) behind everything we do. Having the right answer matters less than understanding *how* you arrived at it. If you memorize a response for an exam, you might forget it. But if you grasp the thought process behind it, you can recreate and refine that knowledge when it truly counts.

### Automating My Life

For me, automation is about more than just tools. It’s about **freeing mental space** for what truly matters. At night, I can simply say, *“Hey Google, goodnight,”* and:

- [Doors and windows](https://www.ring.com/?ref=robweidner.com) are checked
- [Lights turn off](https://www.philips-hue.com/en-us?ref=robweidner.com)
- [Bedroom fans](https://www.boneco.com/en/product-range/air-shower-fans?ref=robweidner.com) and [white noise](https://www.sleepfoundation.org/best-white-noise-machines?ref=robweidner.com) activate
- The [alarm sets](https://github.com/nielsfaber/alarmo?ref=robweidner.com)
- The [BedJet](https://bedjet.com/?ref=robweidner.com) adjusts to 66°F for optimal sleep

That one phrase ensures I wake up **well-rested** and ready to bring my best self to the world.

---

## [Business Sabbaticals](https://medium.com/swlh/taking-a-business-sabbatical-why-you-should-try-it-and-how-to-make-it-happen-31838e89ec82?ref=robweidner.com): A Lesson in Letting Go

This mindset extends to business, too. My partner, [**Rusty Ruthven**](https://www.linkedin.com/in/rustyruthven/?ref=robweidner.com), and I co-founded multiple companies, including [**Film Gear South Africa**](https://filmgearsa.co.za/?ref=robweidner.com), which we ultimately shut down last year. We launched in 2015 to solve a real problem: sourcing professional film equipment in South Africa. The business was **lean** and **automated**, which helped us navigate industry shifts and even COVID. But as the market changed, we reassessed its future.

Inspired by [**Jason Montoya**](https://www.jasonscottmontoya.com/?ref=robweidner.com), we decided on a **business sabbatical**—a pause to reassess without the noise of daily operations. We:

- Informed suppliers we’d be out of touch
- Set up an out-of-office message
- Provided our employee with generous notice and severance

In the end, closing the business was the right decision. Thanks to the [**Profit First**](https://profitfirstbook.com/?ref=robweidner.com) model (more on that another time, but also check out [Relay](https://relayfi.com/?ref=robweidner.com)), we reinvested remaining funds into our other venture, [**ShowCal**](https://showcal.io/?ref=robweidner.com).

> **To everyone who supported us—thank you.**  
> We started Film Gear South Africa to bridge the gap between Hollywood and South Africa, pouring our hearts into it. We never took outside investment or even a salary. The lessons we gained were invaluable—not just in business, but in life.

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## The Magic of *Why*

At the core of everything is the [**why**](https://simonsinek.com/find-your-why/?ref=robweidner.com). When you align with a clear **purpose** and surround yourself with those who share your vision, you create something uniquely powerful. Even if things don’t go as planned, you move forward with **integrity**, **passion**, and **intention**—and that’s what truly matters.

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## Next Steps

I hope this newsletter sparks thoughts on your own [**philosophy fit**](https://hbr.org/2018/08/how-to-know-if-theres-a-culture-fit?ref=robweidner.com), your [**why**](https://simonsinek.com/find-your-why/?ref=robweidner.com), and the path you’re taking in life and business. **Thanks for reading**, and stay tuned for more on [**ShowCal**](https://showcal.io/?ref=robweidner.com) and the power of automating your life—with **intentionality**, of course!

\-Rob