What to do if you feel stuck, how to do an Odyssey Plan and recent book purchases

And other lists I made this week

Welcome to Easy, Breezi.

Your friend who sends you a weekly update on what she's working on, reading through, and thinking about – in a list.

I have one rule to this newsletter, lists only. The only exception is this yellow box. I'll use this to say anything that needs to be said in a full paragraph. I’m writing this as I unpack my bags from Tulum and repack because I’m headed to California this weekend – first time ever!

This newsletter is dedicated to anyone who’s ever felt stuck before

  • If you’re currently in a job that you don’t love while you’re watching everyone around you pursue their passions

  • If you’re in a romantic relationship that doesn’t serve you anymore but you’re not sure how to let it go

  • If you’re no longer excited about the hobbies that used to bring you excitement and joy

  • If you’re living in the same old city you grew up in over the last decade yet feel like there’s no where else to go

  • If you’re in a friendship that you’ve outgrown and those people no longer understand this new season of life you’re in

Here’s the thing: are you actually feeling stuck, or is it something else instead?

  • Trapped?

  • Lost?

  • Scared?

  • Burnt Out?

Wait Lillie, aren’t they all the same thing?

  • No they’re not

  • All 5 of those feelings actually mean 5 different things

  • I used to make the mistake of overusing the word “stuck” whenever I felt like I wasn’t making progress in life

Let me break these 5 different feelings down

  1. Feeling stuck: is like you’re currently on a path you know isn’t right for you but you're also unsure of what path you should be on – therefore you just stay on the current path (even though it’s not right)

  2. Feeling trapped: is like you’re currently walking down a path you know isn’t right for you, and you know exactly which path you should be on, but for some reason (circumstance or whatever) – you can’t leave

  3. Feeling lost: is like you’re currently standing in front of a few different paths but you’re unsure which one is the right one – so you hold off on making the choice

  4. Feeling scared: is like you’re currently standing in front of a few different paths and you know exactly which one is the right one but you’re afraid to take that step – so you hold off on making the choice

  5. Feeling burnt out: is like you see no paths in front of you, no doors, no openings, nothing, it just feels like there’s no where to go

So which one is it? Read that last list again – can you identify how you feel:

  1. Stuck?

  2. Trapped?

  3. Lost?

  4. Scared?

  5. Burnt Out?

💡 When we start to feel negative emotions, we’re quick to assign it a name and move it to the side. The downside to that is we often mislabel or overgeneralize how we feel.

Taking a few minutes to sit with uncomfortable feelings (although it does suck) is necessary before we start to resolve them.

Whether you feel stuck, trapped, lost, scared or burnt out – it’s okay

  • We live life in seasons, some better than the others

  • The goal isn’t to avoid these feelings

  • It’s to sit with them, identify them then try to work on them

  • My goal with this newsletter is share some of the tools and resources that have helped me work through the tougher seasons

Recently, I thought I was “stuck” …

  • For the last two weeks, I’ve struggled with feeling like I wasn’t moving fast enough with Breezi – I didn’t see the progress I had expected to achieve and I felt like nothing was launching quickly enough

  • We had just brought on a dev and all of a sudden we went from “let’s dream up what this product can be” to “okay what is the leanest MVP we can make in the next 6 weeks”

  • Then I realized, I actually wasn’t stuck at all – I was lost

  • Feeling lost: is like you’re currently standing in front of a few different paths but you’re unsure which one is the right one – so you hold off on making the choice

  • My strengths have always been in user acquisition, growth funnels, sales and brand building and now all of a sudden, my role shifted to managing a team of two designers and a dev to ship out our first MVP

  • Making decisions took 10x longer because it took me longer to figure out what the best next step forward was

  • It’s not surprising I felt lost

3 things I did to help myself get out of feeling lost

  • Texted 8-9 different friends in engineering, design and product management to walk me through their process at work, what they liked about it and what they didn’t

  • Asked my mentors to intros to early stage startup CTOs so I can get guidance on how to be better at this role

  • Bought the #1 book on management from Amazon (lol)

Here’s a helpful toolkit for managing uncomfortable feelings

  1. Feeling Stuck → Try Odyssey Planning

  2. Feeling Trapped → Try Future Self Journalling

  3. Feeling Lost → Reach out to mentors and advisors

  4. Feeling Scared → Follow Mel Robbins’ 5 Second Rule

  5. Feeling Burnt Out → Take a break, find time for yourself and give yourself grace to work through it at your own pace

What in the world is Odyssey Planning

  • The idea here is basically to map out three alternative realities of your life over the next 5 years on three sheets of paper

  • In the first instance, you draw/write out your current plan or existing idea for how life will look for the next five years

  • In the next, you figure out what you would do if plan A can’t happen

  • In the third iteration, it’s time for some blue sky thinking — what would you do if money and time were no object?

  • For each plan, you assess to what capacity or extent you have the: resources, confidence, coherence as well as how much you like it

  • Then you give it a name and list any questions you have about this plan

A snippet of Odyssey Planning from early this year*

*If you’re curious to see more of my Odyssey Planning or want me to talk you through how to do this, reply back and I’m more than happy to share :)

My results were:

  • Scenario #1: Tech startup founder with rising success

  • Scenario #2: Launching creative brands across the world

  • Scenario #2: Production studio sharing stories and knowledge

💡 I found Odyssey Planning a helpful way to project into the future and a very valuable activity for presenting myself with three unique and possible options for what life could look like.

It requires you to think from a visionary and imaginative perspective, entertaining the “what ifs” of existence, but also specific and concrete, plotting out the “how tos” as well.

A great exercise for exploring where you want to go next.

Here’s what my calendar looks like for the next month or so

  • 5/14 to 5/18 – Working from San Diego (send recs!)

  • 5/19 to 5/21 – In Vegas for a music festival

  • 5/28 – I’m turning 25 woo hoo 🙆‍♀️

  • 6/20 to 7/22 – Subletting an apartment in NY for the month

Tweets and articles I think everyone should read this week

If you found anything in this newsletter helpful, I'd love to connect on Twitter – tweet me a screenshot of your favorite part and let's chat 👋

I'll be back next week with more lists!