The 5 Questions You Need To Ask To Take Ownership Of The Changes You Want To Make



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Today At A Glance

  • Sharing wins

  • The 5 Question Framework

  • The Break Job Board

  • What’s happening on the Podcast

Sharing Wins I keep plugging away at my side hustle Quotebook. Even though I feel like progress is slow, we’ve had a couple nice wins recently:

  • We made CNN.com’s list of Best Travel Journals. While this isn’t the first use case, I’ve heard from family travelers that it’s a great way to capture some of their experience on a trip!

  • We signed up our first physical retail seller! I had been really trying to figure out online ads, but I’d say it all fell flat. I kinda hate Facebook even more than I used to. So I pivoted some energy to learning about retail. Cloth and Metal Boutique in my hometown loves the product, and we’re now on the shelves.!

I’d love if you would share some of your wins! Shoot them over to me on twitter or Linkedin (links above) and I might share them in the next issue!

The Only 5 Questions You Need To Ask As a guy juggling multiple projects/priorities/goals in all phases of life just like you, I struggle (very often) with where to put my time and energy.

I’m in constant re-evaluation mode. Stuck floating between seeing the field and playing on the field.

At least every 6 months I hit a "reset" moment where I question everything I'm doing. Am I working on the right priorities? Do I believe that what I’m doing will work? How can I make this all easier? Is this new thing a real thing, or just the next shiny object? How do I know when this is working, when to stop or when to double down?

Multiply these questions times all the phases of my life (family, friends, work, health, mission) and you can see how I get overwhelmed. I’m betting you feel it too.

It’s hard to ‘systematize’ all of this, but building a self reflection process can help. When people want to change, most think of what they want to add, but stopping something can be even more powerful.

In these ruts, we also need to acknowledge what we are doing well and what we want to continue. This is key to framing our habits and abilities in the right light to avoid constant negativity.

I found a simple 5 Question Framework (h/t to @toddherman) that helps me assess, identify and target changes.

Todd says that anything in life is about deciding one of 5 things:

  1. Start something

  2. Stop something

  3. Continue something

  4. Do more of something

  5. Do less of something

Lets break down all 5 Questions.

1. What do I want to start doing? This is usually the easiest place to start. You’ve had a trigger tripped in your mind and you’re ready to start something different. It may be building a habit that you don’t have yet, it might be starting a new career, building a product, building an audience, or acquiring some skill.

You’re not doing it now. You want to start doing it. List them all out. Here are mine:


2. What do I want to stop doing? Stopping a negative habit is often more powerful than starting a good one because removing something frees up more time and energy for you to redirect into more productive activities. Stopping an activity and starting an activity are sometimes two sides of the same coin. For instance, I could say I want to start eating healthy, or I could say I want to stop eating crappy food.

Maybe you want to do both. List them out. Here are mine:

3. What do I want to continue? This question forces you to think about some of the good things that you do. When I’m spinning my wheels figuring out where to invest my time and energy, I need the reminder to look at myself objectively instead of getting down on myself. This question helps.

Here is my list:

4. What do I want to do more of? This question is different than what do I want to start. You do these things some time, and you want to do more of them. You can’t do them all the time, but doing more would make you happy. For instance, I love a good nap, but it’s not like I can nap all the time. set a realistic target increase in a behavior and see how much happier that makes you.

Here is my list:

5. What do I want to do less of? This question is for all those things that you can’t cut out completely, but you’d definitely benefit from doing less. The biggest one that pops into my mind is “less meetings!” Meetings are soul crushing, so I’m always trying to figure out ways to decrease meetings.

Here is my list:

How do pros incorporate these questions? Some of the most accomplished and productive people I know and follow use some sort of yearly review at a minimum, and many have a quarterly or monthly process as well.

Specifically for the more of/less of questions - at the end of a year, take a look back at your calendar and jot down the people, activities or commitments that are either positive or negative for you. Then for the next year simply schedule more or less of those things! SIMPLE.

I got this approach from @timferriss here.

The Break Job Board I teamed up with Pallet to create a curated job board for our community! These jobs are tech focused, remote first opportunities. I’d love it if you followed. Maybe, just maybe you’ll find your next big opportunity here.

Here are a few featured opportunities:

Also, If you’re looking to support the community and have a job to post, you can do so by clicking the ‘Post a Job’ button.

What’s happening on the pod? I got to talk to Tom Brunskill, CEO of Forage a job simulation platform that helps students bridge the gap between education and work opportunities. Tom co-founded Forage in 2017 to provide the ability to preskill through virtual job simulations produced by the world’s top companies, including J.P. Morgan, Lyft and Walmart, to name a few.

Watch here or listen here. Please like and subscribe if you find this conversation valuable.

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