20 Years Old, 5 Businesses Later… Here is What I’ve Learned About Making Choices

Posted a year ago

When should I start my business?
Is this the business I should be building?
Should I partner with these people?
Should I advertise on Snapchat?
What about Twitter?
Musical.ly, what?
I’m selling online already, should I get my product into stores?
Should I open a brick and mortar storefront?
Should my business expand to another city?
Should we use Squarespace, Shopify, or build something ourselves?
Do I need an app?
When should I hire?
Should that person get fired?
What should I do?
What am I even doing?
Where am I going with this business?
What is even going on?

Every entrepreneur has thousands of questions running through their mind and hundreds of decisions to make. The only thing an entrepreneur does is make decisions, and execute on them — whether themselves or hiring someone to execute for them.

Decisions, decisions, decisions; there’s no escaping it.
We, as entrepreneurs, have to make thousands of decisions and make them fast, every day, with never enough information for any person to be comfortable. That’s what makes people building anything at scale unique: the ability to make fast decisive decisions in the face of uncertainty.


I considered writing this introduction at the beginning of this article, but saying, ‘Hi,’ didn’t seem as catchy as listing twenty-one questions; nonetheless, I figured, before I go on and help you solve your choice paralysis, I’d introduce myself.

I’m Jeremy Becker. I’m an entrepreneur based in Kelowna, BC, Canada. My childhood was spent selling whatever I could to make money. I spent my teen years building various businesses, which you can read about here, here, here, and how they failed here and here.

I believe in luck. You didn’t do anything to be born. You took no part in choosing your parents or where you’d have your childhood. That was luck. In business, nothing happens by accident. I believe there are opportunities and our ability to capitalize on the right ones creates success.

Work sets you up for these opportunities, it’s up to you what you do with them. No one will knock on your door and offer you your dreams. It simply doesn’t happen.

Sidebar: even if it did, would you want it? Would you want your dreams without the hard work? I don’t.


So here we are. We know we need to work, we know we need to capitalize on the right opportunities, we know we have so many decisions to make that we don’t know which ones to make. What do we do? Luckily there’s a solution. It doesn’t make it black and white, but you can consider it like fog lights cutting through the mist; they’ll help keep you on the right track.

Initially, when I’m facing a decision, I run it through two filters in my mind.

  1. When I’m 90, what would I not regret, or regret the least; doing this, or not doing this?
  2. Do I have any intuitive gut feelings about this?

I compare the two and get started based on that. Usually, it’s about 40% question A and 60% question B. I strongly value intuition.

Sometimes things make sense on paper but don’t feel right.
You might be reading this and thinking, ‘okay, Jeremy, sounds great. But can you give me something more practical and applicable?’ Yes! Yes, I can.

Strategic Planning

I’ve always believed that when you know where you want to go, and you know why you’re doing what you’re doing, every decision is simple because you can lay it next to your goal and see if it helps you get closer or not. That is the foundation for this next part. But I’ll walk you through how to discover the Where and Why.

A few months ago, I was in a meeting with a personal mentor. He was talking about the strategic vision for his organization. He separated it into Mission, Vision, Core Values, Strategies, and Tactics.

The first two parts, Mission and Vision, are decided by the founding team. These don’t change; they evolve with the founders. It’s the core of the ‘Why’ you’re doing what you’re doing.


The mission is the why you do what you do. What are you trying to accomplish at the highest level? Think about this as your biggest north star. It’s what drives you over the next 40, 60, or 80 years of your life. It has to be something close to your heart that you’re passionate about that makes you get up every morning.


In short, your vision is the moment in your mind, a scene, a picture of what you’re trying to accomplish.

Maybe you’re a musician. Your moment could be standing on the stage. Everything is dark; pitch black as a murmur creeps through the 50,000 people waiting to watch you play. As you start, the lights turn on, and a roar of energy and excitement fills the stadium.

The purpose is to have the picture of your future as clear as day. What do you want your future to look like? What is it that you’re trying to build? And have that real moment you can go to in your mind for some inspiration.

The next part is a little bit more flexible. You and the rest of the leadership within your company discover these. Initially, in established companies these aren't fabricated or created, it’s what’s already happening in your business. Once they’re discovered, you can make efforts to evolve them.


As you build your company, you will discover what you value. It’s important to differentiate what you actually value with what you wish you valued; words vs. actions.

My personal values are empathetic communication, integrity, and execution.


This section fits partly into decisions made by leadership within your business and employees within your business.
Strategies are how you plan to accomplish execute on your mission. For example, the strategy could be to become known as a thought leader in your industry.


The tactics are how you implement your strategies. They can change overnight. You have to adapt your tactics to the realities of the marketplace. You can’t sleep on these; you have to keep trying.

As Gary Vaynerchuk would say, this is “the dirt”. Everything else has been “the clouds”, but this is the nitty gritty. How do you plan to become a thought leader? You create a podcast and distribute it on iTunes, Overcast, Facebook Video, Youtube, and Soundcloud. You create micro-content to drive people from your Instagram to iTunes. You execute on Instagram Stories and Snapchat Stories.

Once you have laid out your Mission, Vision, Values, Strategies, and Tactics, you can take any decision and run it through the filter. Here is my approach:

  1. Does X in any way help me accomplish my mission?
    Yes? Does X fit into one of my current strategies?

    -- Yes? Great. Design and implement tactics for it.

    -- No? Let’s create and re-evaluate strategies.

    No? Do other people on the team champion X?

  2. When I’m 90 what would I not regret, or regret the least: doing X, or not doing X.

  3. Does this feel right or not? (Intuition)
    Yes? Do it.

    No? Don’t do it.

    Not sure? Explore it more, and revisit a set date later.

This is the approach I use to make all my decisions. I have a personal version of this list and a version for every business I build. I truly believe by knowing all these parts you’re able to streamline your decision-making process and execute much faster.
There is so much value in moving fast. Stop debating, just make shit happen. There’s no one but you. It starts and stops with you.

I really hope you found value in this post! If you did, share it with your friends :) if you’re interested in more I have to say, you can follow me around the interwebs under @iamjbecker.

Originally posted on Serial Disruptors

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