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How do I design my startup around my life?

TL;DR: “I'm hearing all of this talk about Founders working remotely on their own schedule, traveling, and enjoying life while growing their amazing startups. Meanwhile, I'm working 80 hours a week in a cramped office and the only thing growing is my waistline. What am I doing wrong?"

Building a startup that drives our lifestyle choices is incredibly hard, no matter what that care-free Founder's Instagram might suggest.

In order to make our startups work around our lifestyle, we have to make a deliberate choice to bend the fabric of reality to meet our demands. It's crazy hard. But it can actually be done.

Today’s Advice Sponsored by Microsoft

It Starts With Strong Commitments

The foundation for having a startup that supports our dream lifestyles is making really strong commitments to those lifestyle choices. For example, if we're parents and we want to make sure we never miss our kid's soccer game, we have to publicly make that commitment and stick to it.

Sometimes just announcing those commitments is a great way to get the ball rolling. When we launched we had all just had our first kids, so we made a proclamation that we would never let the business get in the way of our families. 8 years later we've never broken that promise, largely because it was committed to very publicly, so we could all actively support it.

Take Baby Steps — Then Commit

Where we blow this up as Founders is when we try to take it too far too fast. No, we probably can't work from a beach in Fiji for 6 months out of the year (yet). But can we try working remotely for a solid week? A big part of shifting our workflow and culture is just making small, consistent steps toward adjusting the company to fit our goals.

When we wanted to create more flexibility at, we started by just trying one Wednesday where we could work from home. It was easy to try and easy to reverse if it didn't work. Now, over 200 people work remotely and we're more efficient than ever. Those baby steps are what made it possible.

Bring Personal Goals Into Corporate Planning

All too often we separate our "startup goals" from our "personal goals" as if they’re not allowed to intermingle. But really, our startups often ARE our lives, so separating the goals and activities doesn't make any sense.

What's worked well for us at is that we sync our personal goals first (commitment to our families, free time to pursue interests, how we want to help people) and then figure out how our business can support those goals. We make daily decisions based on that compass, and our lives reflect that.

Lifestyle Design Isn't a Myth

There's very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

Life is too short. If we're going to create something beautiful in the world with our startup, there's no reason we can't build a beautiful lifestyle in the process.

Hi. It’s Bobby.

If you’ve learned anything about me from the ads I write for The Hustle Daily, it’s that I’m, uh… all over the place (to put it nicely). 

  • I frequently oversleep and get lost trying to find shortcuts to work

  • I often take last-minute, unannounced trips to Indiana to stare at my nephew

  • Sometimes I go for a run at 12:00 and forget I have a meeting at 12:05

All that to say, it’s pretty clear our ads team here at The Hustle needs a special kind of communication software to keep up.

For that, there’s only one choice: Microsoft Teams

Whether I’m stuck working at a Starbucks in Indianapolis or sweatily taking a meeting on a public bench post-run, Teams allows Meg and I to seamlessly exchange everything we need to keep those ads crankin’.

With Teams, we can handle tasks, drafts, feedback, and edits, all within one simple platform… not to mention sharing GIFs when it feels like the ad-valanche is about to overwhelm us (hey, you can’t put a price on your sanity).

So, what would happen without it? 


I’m just gonna ignore that question. I’ve got a flight to catch. 

(P.S. Meg just messaged. I forgot the CTA -- Try Teams today! It’s free!)

Teams run on Teams →

In Case You Missed It


I’m Killing Myself. How is Everyone Else Finding Work/Life Balance? We're supposed to believe that we can build a world-changing startup from nothing while simultaneously traveling to exotic places and enjoying our "best life". For most of us, that just doesn't add up. What's blowing us up, though, is how we approach the problem.

Work From Home (podcast). Is remote work bullsh*t? Or can remote work & work-from-home policies actually have a positive impact on your Startup? Join Wil and Ryan as they break it down.

How to Mix a Family and a Startup. How do we create a proper balance between growing our family and growing our startups? Do we have to swim in a sea of guilt through this entire journey or is there some other way to get ahead? 

Thanks from the Startups Team,

Wil Schroter
Founder, CEO and Startup Sensei

Ryan Rutan
CMO and Man with the Golden Podcast Voice
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