Test Your Ideas (And Assumptions)

Lately, I’ve been playing around with the idea of creating a Monday Mailer podcast featuring audio versions of my articles, along with occasional original content. I’ve dabbled with audio projects in the past, but never on a regular basis. It’s an exciting idea, but I’m most definitely an amateur when it comes to this sort of thing.

It can be scary to try something outside your comfort zone, whether it’s a side project, added responsibilities at work, or a new hobby. You’re putting yourself out there, raw and vulnerable. But if you don’t push your boundaries every once in a while, you’ll never grow.

I have no idea if my podcast idea will be well-received. So, instead of jumping in with both feet, I’m reframing the concept as a simple test. There're a few questions I’m hoping to answer:

  1. Is a podcast something my audience wants?
  2. Do I have the ability to produce a quality episode, each and every week?
  3. Can I speak in a way that’s warm and inviting, rather than annoying?

Instead of committing lots of time and resources to trying it out, I’m putting on my lab coat and testing a hypothesis: “I can produce a podcast episode that people will enjoy listening to.” You can take this approach in your work, too.

Break your idea down into the smallest possible version of itself. Ask yourself:

“What’s the least I can do to test this out in front of real people?”

Cut everything else out and share it with the world. Right now. It isn’t easy – you’ll worry it isn’t polished enough. But that’s the point. If your audience doesn’t “get it” in the rough stages, it’s unlikely a few extra hours of work will change their minds. You can always improve it later if the feedback is positive.

In my case, I recorded a quick test track – around a minute and a half long – and put it up on my website. I added a quick, anonymous survey and tweeted out the link. So far, the feedback has ranged from “This is awesome!” to “You sound like you’re copying Ira Glass.” Some of the more critical comments sting a little, at first. But I’d rather hear them now than ten episodes down the road.

It’s important that we separate ourselves from our work, sometimes. Don’t hold any idea so tight you can’t make changes or move on if needed. It might take 100 failed experiments before you find something that works. And that’s okay.

Real success isn’t hitting it out of the park with every at bat. That never happens. Real success is spending your time on what matters and making the most of it.

Making Time for Side Projects

This week’s article is as much a reminder to myself as it is advice for you. I haven’t done a good job of managing my time, lately. Instead of writing or pushing my side projects forward, I’ve been binge-watching Netflix, reading blog posts full of productivity tips, and playing copious amounts of Pokémon Go.

Time to re-focus.

Here are some tips for making more time for your side projects. I’ll be re-implementing a bunch of them myself, this week.


Do everything you can to control your schedule, free of interference from other people. When you do creative work, you need extended periods of uninterrupted time to focus. It’s up to you to create that time.

If someone walked up to you and asked for $100, you’d rightfully have questions. But we rarely apply the same standard to our calendars. Don’t blindly accept every meeting request you receive. Figure out when you’re most productive and schedule around those times.

Granted, this can be difficult if you work at a full-time job or have family commitments. Those hours are accounted for already. But there’s lots of wiggle room if you’re intentional about how you spend the rest of your time.


I know it’s a bit ironic for me to suggest this, what with running the Monday Mailer and all. But, at a certain point, you have to stop consuming other people’s content and start creating your own. Articles full of tips & tricks, productivity hacks, and other bullshit can be helpful – for a while.

But every second you spend learning about productivity is a second you aren’t, well, being productive. How often do you apply what you’ve read to your work? Almost never, if you’re anything like me. It’s a trap.

Once you’ve read something valuable stop, think about how you can apply it to your life, then close your browser and go do it. Favour action. You’ll learn more that way, anyway.


Often, out of a sense of obligation or guilt, we commit to doing things we hate. It doesn’t just eat up your time; it erodes your overall happiness and satisfaction. Derek Sivers put it best: “If you’re not saying ‘HELL YEAH!’ about something, say ‘no.'”

Cancel any commitment you aren’t 100% invested in.


Sometimes the hard part isn’t making time for your work; it’s getting started once you’re staring at a blank page. It isn’t always easy to turn free time into productive time (see: my Netflix binge-watching). The more you can reduce the effort it takes to get down to work, the better.

As you’re wrapping up your day, ask yourself one question: “What’s something I can do – right now – to make it easier to do my work tomorrow?”

It could mean cleaning off and organizing your desk. Or writing a to-do list. Or deciding on your next writing topic. It will be unique to you and whatever you’re working on right now. It’s a habit you’ll have to work on developing, at first. But once you do, you’ll thank yourself each and every morning.

What's Your North Star?

On a clear night, with just the right conditions, there’s about 6,000 stars visible to the naked eye. As far back as the 2nd century, human beings have looked to those stars to help determine their location and heading. And none is more well-known than the North Star.

The North Star has one unique property: it never moves. Okay, that isn’t strictly true. But for all intents and purposes, you can count on it staying put — right above the North Pole. If you were trying to navigate in the days before GPS, knowing which way was north turned out to be pretty handy.

When it comes to doing our best work, I think we all need our version of a North Star — something that reminds us where we’re going and what we’re trying to accomplish. My North Star is “Be Useful.” When I’m feeling lost, unsure of what to do next, or stuck, I know I can’t go wrong trying to bring value to someone else.

I’ve said before that procrastination is a byproduct of fear. Fear of failure. Fear of other people's opinions. Fear of not being “good enough.” But I think there’s another angle.

Procrastination is forgetting our North Star.

When we get stuck on a project, it’s helpful to remember why we started working on it in the first place. Most of my early side projects were a response to a job I hated. The work was uninspiring, the clients were awful, and I wasn’t learning anything new. I knew I wouldn’t be able to get a better job with the kind of work I’d been doing. So one night, at the peak of frustration, I said “fuck it” and started coding. I realized there was only one person who could change my situation: me.

You’d think that would be sufficient motivation to carry me through to the end of the project. But it wasn’t. There we so many nights where all I wanted to do was flop onto the couch and watch TV. But it didn’t take long before a tiny voice in my head spoke up.

“I thought you wanted more than this?”

Once I remembered my purpose — my North Star — it became hard to justify six hours of TV on the couch.

Your North Star can be anything that speaks to the heart of why you started a side project in the first place. Landing a more fulfilling job, satisfying the creative half of your brain, improving your skills, or creating a better life for those you love.

No one can tell you what your North Star is. It’s something you have to decide for yourself. So decide, right now. Write it down and put it somewhere you’ll see it every day.

And when those dark, tired moments happen — and they will happen — take a look at that piece of paper, and remind yourself of what drives you.