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Hi Reader,

I’m a sucker for a good side quest.

In video games, there’s usually (at minimum) 2 types of quests:

• Main Story Quests - these are the things that you’re doing that progress you towards completing the “main” goal of the game (eg: free the land, solve a mystery, etc)
• Side Quests - these are things you do that generally don’t progress the story forward, but they’re fun self-contained mini missions you can opt into (eg: Tom went out hunting 2 days ago and never came back, can you figure out what happened to him?)

The more time I spend running a business with Jo, the more I’m convinced that entrepreneurship is just one big game (with life-altering rewards & consequences).

• Games have levels -> Business has phases (side hustle, building, scaling, hiring, etc)
• Games have skills you level up -> Business has expertises that you learn
• Games have characters (those who help you, those who guide you, those who try to stop you) -> Business has a network of people (clients, educators, haters)
• Games have other players (your squad or party) -> Business has your community or peer group (or The Breakroom?)
• Games have quests -> Business has projects or goals

If you accept that business is a game, why would you ever spend time on a side quest for your business?

You’ve heard us preach the importance of having a North Star and making sure that everything you’re doing is working towards your big goals. That you shouldn’t be getting distracted or slowed down by things that don’t get you closer to your goals.

For me, there are a couple of (good) reasons to spend time on side quests:

1. Skill Development - sometimes you need to build up your expertise before you take on your next “main story quest”, so you take on a few side quests that are a great way of building or leveling up another skill (eg: taking on contract work under an expert in a field you want to know more about, while it’ll pay you lower than your desired income, the training you’ll learn from them as an employee is invaluable)
2. Spending Time with your Crew - just because we’re all playing the same game of business doesn’t mean we’re in the same place of the main story line, sometimes side quests are a great way to work side by side with a few good friends on a short term project and cement new friendships (eg: hosting a retreat with a few friends even if you don’t have a community based business model)
3. Test Your Metal with Low(er) Stakes - most video games have some form of “boss battles” every so often. Maybe you want to practice a combination of skills, armor, or weapons out in a lower-stakes way before taking on a big boss. The same thing can apply to business if you want to test out a process or template before integrating it into your flagship offers and risk messing up something that works.
4. Break Up the Sameness - some games that many of us played in the mid-2000s (ahem Runescape or Sims) have a reputation for just grinding (doing the same thing over and over) to level up skills. And that can honestly get boring sometimes. This is a great time to do a side quest, to break up the monotony and focus on something that has a clean “container” or start & finish point that you can check the box of completing something.

This year has been an eye-opening experience for me in starting to see the “rewards” of taking on so many side quests over the years. It feels like each week we have a coaching conversation where we can share expertise through the lens of a personal experience since we’ve personally tried something very similar to the thing someone is asking a question about, and learned that it wasn’t a main story quest for us…

For example, these are all side quests we’ve taken over the years that have better prepared us for the main story quest we’re on right now:

• Years ago, we ran a paid membership for 6 months that did mid-4 figures in income before we shut it down
• We’ve started (and closed) 2 marketing agencies over the years, one just the two of us, and one with a contractor - both times we did high 4 figures, proving that it was a working business model before shutting them down because it wasn’t the right business model for us
• We snowballed ourselves to a 4-figure brand partnership
• We’ve been paid to do almost all the photography types (wedding, real estate, couples, elopement, graduation, maternity, branding, product, boudoir, short term rental, and more)
• We tried being travel YouTubers for 4 months
• We had a podcast with thousands of lifetime downloads
• I worked in corporate
• I spent a week walking Hollywood studios, networking my way towards a job in film & television
• I went to Thailand to consult with a hammock company
• I spent months leading a software feature rollout at a manufacturing company

The thing is, all of those things that feel like they’re random side quests have shaped us to be better coaches, our current main story quest. If we just look at the bottom three points before I joined Jo in our company;

• Leading a software rollout taught me TONS about change management & how to communicate with people who are very resistant to change - directly applicable to how to teach people to deal with client problems today.
• Working with a hammock company taught me to take a holistic view of a small business - because one person was wearing all the hats and we had to show him where his blind spots were.
• Before my week in Hollywood, I spent a month reaching out to people I had any connection with (alumni, friends of friends, random connects, etc) and setting up face-to-face - this is a huge skill now that we’re growing a community-based business, doing more outbound connecting, and building rapport quickly.

A word of caution, tho - you can actually take on too many side quests.

Just because they’re fun, you learn valuable things, and you can make the justification that it’ll be helpful later, doesn’t mean you should say yes to it. Because every moment you spend on a side quest is a delay to the main story quests in your business.

My advice - before you take on a new project, task, or launch - take the time to zoom out and consciously decide for yourself, “Is this a main story quest or a side quest?”

Just knowing what type of quest it actually is will help you make a better decision if it (whatever it is) is worth your time right now. Because what most people (me included) forget is that you can almost always come back and do a side quest later, it’s not like it’ll disappear if you don’t do it immediately.

This week Jo & I are doing our 2025 recap and 2026 planning in preparation for doing a 2026 planning masterclass in The Breakroom in a few weeks, and even though we’re only halfway through the conversation, it’s bringing clarity for me around what are going to be my main story quests next year.

If you wanna know more about The Breakroom (games are more fun when played with friends) or be part of that masterclass next month, you can see all the details here or send us any questions in a reply or DM on IG.

Have a great Thursday!

Lyndon

Ps can you do us a huge favor? If you made it this far in the email can you hit reply and let us know what your favorite side quest you did this year was?