Sure, It’ll Be Risky But The Reward Is Huge

What Works with Tara McMullin

Theoretically, we all know that starting and running a business is risky.

But we often behave as though there’s a way to eliminate all the risk.

Every time we wait to launch a product until it’s “right,” every time we hesitate to change things up with our content because we want to do it the “right way,” every time we delay hiring a new team member until the “right” time…

…it’s our way of mitigating risk and opting for certainty.

Unfortunately, it’s rarely the people who wait for the “sure thing” that really prosper.

Now, I just listed some fairly big decisions that business owners make on a regular basis.

But there’s risk in our every day actions, too:

  • You could send out a pitch to 3 podcasters as soon as you’re done reading this email–but that would be a risk
  • You could share an invitation to your program with someone who know would be perfect for it–but that would be a risk
  • You could email a colleague and ask for help on your current project–but that would be a risk
  • You could hand over a bigger piece of the work to your team member–but that would be a risk

Sure, each of these actions could be met with silence or create a mess for you to clean up.

But the upside is huge: you could land 3 interviews, close a sale, get a fantastic idea about how to move forward, and save yourself 3 more hours per week.

Over the last month, I’ve been looking for all the tiny risks I can take during my day.

Every time I find myself hesitating because I’m not sure about the next step or the right action, I pause and ask myself which option has the greater potential for reward.

Which one, despite the risk, could end in me getting exactly what I want?

Then, I do that thing.

Now, I really wish I could take credit for this particular mindset shift. But I can’t.

It came directly out of a conversation I had with my friend, Charlie Gilkey. Here’s what he told me:

There are these little “c” moments of courage that happen every day through email conversations, conversations with your clients, with your partners, with your teammates that, taken cumulatively, create a courageous life.

Look at those micro moments in your day and choose the option that requires a little bit more vulnerability.

Choose the option that may not work out. Choose the option that increases uncertainty rather than decreases uncertainty. Choose the option where the comfort would dictate one way of going and growth would dictate another. If you choose those in those email exchanges, if you choose them in the conversations with and customers, if you choose them in conversations with teammates or partners, it can make a world of difference.

Sure, it’ll be risky. But the reward is huge.

Listen to my full conversation with Charlie by clicking here.


This month on the What Works podcast, we’re talking about resilience. And to kick things off, I brought in a guest interviewer to ask me about the how we make things work at What Works–and the long & winding journey it took to get here. If you want the inside scoop on a myriad of mistakes I’ve made and how I bounced back from them, listen to this episode.

🎧 Click here to listen.


Resilience isn’t just a nice-to-have personality trait. It’s a tactical, get-things-done strategy. I talked with the brilliant Charlie Gilkey about how he operationalizes resilience to finish the projects he starts. Charlie and I also talk about the tension between mastery and growth, why we love structure but still crave novelty, how we let conflicting patterns mess with our ability to create results, and why achieving success isn’t just a matter of intelligence or information.

🎧 Click here to listen.


Every business owner needs a break from time to time. But what’s the best way to structure your time away so that you come back primed for action? I found this piece by Tim Harford really insightful. It explains why I really like trips like the one I took around New England this summer, only spending a few days in each location to do 1 or 2 really cool activities. If you haven’t already, start planning your end-of-year time off now but read this article first.

👓 Click here to read.


The What Works Team has been hooked on Notion since January. We’ve completely switched over from Asana, plus we’ve eliminated AirTable and Evernote at the same time. Notion has allowed us to bring the podcast, The Network, and our marketing all together so that the whole team knows what’s going on and the business runs as cohesively as possible. And how did we figure all this out? Marie Poulin. Marie is hosting weekly Notion Office Hours and this week it’s on building a second brain. Check it out!

🖥 Click here to save your seat.


Believe it or not, social media platforms aren’t a competition of who can come up with the pithiest quote or most derivative advice. They really can be a way to make genuine connections, share true stories, and built authentic credibility. But we’ve got to stop pretending that [we have it all figured out, we invented the ideas we’re sharing, we’ve made it, etc…]. Maggie Patterson is pleading with us all to stop pretending and start being real.

👓 Click here to read.

Cover of What Works book by Tara McMullin

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