Posting my Five Year Plans

I just finished creating a page for my five-year plans and updated my “now” page to detail my quarterly and annual goals.

Will it Fly?

This was largely inspired by a conversation with a friend after doing the first exercise in Pat Flynn’s book‌‌ “Will it Fly?”. He had decided to go through the exercises in the book as a way to come up with a highly-aligned business idea that we can work on together with another friend. I’m excited to continue going through the book as well, and will post some takeaways as I‌ do.

I‌ was nervous to share my five-year plans with him. Five-year plans tend to be a little ridiculous. You consider the absolute best-case scenario, and sometimes it feels a little delusional. I‌ struggle with striking the balance between audacity and pragmatism. Too audacious and you’re living in a fantasy. To pragmatic and you’re not going to care about your plan.

But after we discussed each and every point on our lists, including the audacious ones that made me cringe to say out loud, I‌ realized something. If I’m afraid to say something out loud, how will I‌ ever hope to create it in real life?

Fears and objections

I’m afraid of sounding stupid, delusional, ridiculous, greedy and narcissistic. But if my five-year plans make me feel that way, it means I’m not properly aligned with them.

(Note that I’m calling them “five-year plans”, not “five-year dreams”. Dreams are all well and good, but they feel very someday. Everything on my list is something I’m working toward in the real world. These are ideas I’m bringing into physical reality – dreams tend to live in your head.)

If I‌ was fully aligned with everything on my list, there would be no inner resistance to them. I might feel challenged by them, but I’d know on a gut level that I‌ was absolutely capable of them.

Upgrading my character

Part of setting audacious five-year goals is becoming the type of person who resonates with those goals. It’s about getting rid of all the mental boundaries around them. It’s about transforming thoughts like, “this is delusional” into “this is a stretch but absolutely within my capabilities”. It’s not so much about taking action – though that’s a massive part of it – but transforming who‌ I am and how I‌ think.

That’s what excites me most – pushing my own boundaries, raising the ceiling, and growing my character.

Practicing courage through transparency

As such, I’ve decided to publicly share my five-year plans on this blog and write about the process. One thing I‌ love about Pat Flynn is how transparent he is with his business – his monthly income reports are downright inspirational. I want to be transparent about my life’s journey in hopes that you can find inspiration here as well.

My gut lurches a little at sharing this so openly, but it’s an opportunity for me to lean into courage, my primary word for 2020.

I‌ hope you’ll share the journey with me. It’s going to be a ride. 🙂


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