Most business people find themselves on a corporate conveyor belt with a singular direction: upward. A traditional career is akin to climbing a precariously steep mountain. Every step matters, and one misstep—like taking a sabbatical—could send you tumbling down the career ladder while you watch others scamper past you.
By contrast, a career as an entrepreneur is a series of peaks and valleys. As a founder, you aren’t bound to one mountain. Instead, you have the freedom to climb a peak, plant your flag, and then descend into the valley below to rest, reflect, and rejuvenate. And when you’re ready, another mountain awaits.
The ultimate peak is selling a business. After pouring your soul into a venture, there comes a point where you might decide to let it go, not as a sign of giving up but as a strategy. Selling allows you a well-earned respite, a pause to bask in your success and recharge your batteries. In the corporate world, such a hiatus might spell the end of your upward trajectory. But as an entrepreneur, it’s your ticket to freedom, rejuvenation, and perhaps the next big venture.
This week, we dropped an interview with Rob Walling who embodies what it means to live a life less ordinary. Having built an innovative email marketing software called Drip, he didn’t cling to it indefinitely. At the age of 41, Rob sold Drip — some might say too early — but they are missing the point. Selling Drip allowed Rob to take a breather, and then re-invent himself as an investor, author, and guide.
Inspired by Rob’s story, here are five ways to embrace the rhythm of entrepreneurship:
- Get Out, Before You Flame Out
Rob had a successful exit from Drip, but he almost left it too long. He’d been working at Drip for just over 5 years when the business started to take its toll. Short tempered with his wife and unavailable at time for his kids, Rob pulled the rip cord and sold Drip when he reached the 10 employee milestone. Since then, Drip has gone on to generate tens of millions in revenue with hundreds of employees under new ownership, but Rob doesn’t regret selling, “maybe I could have sold for two or three times more, and maybe I would be divorced.”
- Take 6 Months To Play
After leaving Drip, Rob took six full months off to play and explore. He received a subscription to Masterclass as a gift, and took a series of courses. He picked up his guitar again and played more chess. He resisted the urge to lock into anything new, giving his mind time to be creative.
Listen to Rob’s wife, Dr. Sherry Walling as she describes the importance of play time after selling a business.
- Take a Long Walk in The Bush
Next, Rob took a couple of days for a “founder’s retreat” during which he spent time completely alone. No phone, no family, just Rob and his answers to questions he asked himself like:
- “What have I loved doing my whole life? What have I not?”
- “What do I want this next act to look like? What do I not want to do?”
In this clip, Rob explains how his founder’s retreat gave him the clarity to decide what to do next.
- Figure Out What Makes You Tick
At some point, you will want to figure out the essence of who you are and what makes you tick. In Rob’s case, he realized he was happiest when he was learning and creating so he knew that whatever he decided to do next, he wanted it to be something new where he could be creative.
- Get Back in The Game
There will come a time when exploring hobbies is no longer fulfilling which is when you know it’s probably time to get back in the game with your new-found insight about what makes you feel alive. In Rob’s case, he has always enjoyed podcasting and mentoring software entrepreneurs so he doubled down on his podcast and community of entrepreneurs and also started Tiny Seed an accelerator where Rob and his partners invest in promising SaaS companies.
Entrepreneurship isn’t just a career choice; it’s a way of life. It enables you to define your pace, choose your challenges, and celebrate your victories in ways a conventional career seldom allows. And sometimes, the bravest move isn’t climbing another peak—it’s knowing when to descend and prepare for the next ascent.
📣 Quote of the Week
“I was able to exit for enough money that I didn’t have to work again. And that obviously created an interesting paradox of choice.”
– Rob Walling
🔨 A Tool to Help You Exit
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If you know a founder who has successfully exited their business and has valuable insights to share, we encourage you to nominate them.
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