You hit a wall on the main project. The engine is still running and you have nothing left to give mentally, and pushing harder would drain you while checking out would leave you restless and unsatisfied. A side quest is the third option: permission to work differently for a couple of hours, on something that refuels you. Jess found hers in a group chat with two friends. She built a personal brand repository, 49 tabs of AI prompts for every major piece of a brand, and came back to a five-hour intensive with more capacity than she left with. This check runs your detour through the same three questions before you go, so you can tell a real side quest from avoidance wearing productivity clothing.
Name the two quests
A side quest only makes sense next to the main thing. Name both, even roughly.
Cannot think of one? Mission Detour, the tool Julia built from this same conversation, generates side quests from your main quest. It is free to start.
Question 1: Is it generative?
A side quest makes something. Avoidance consumes things. That is the hard line. At the end of the time you spend, is there something new that did not exist before?
It makes something (pick any that fit):
Or is it really this (pick any that fit)?
Question 2: Is it adjacent?
Adjacent means it lives in the same ecosystem as your main quest, even if it is not the main quest itself. A side door in the same building, not a different building.
Can you explain the connection in one sentence without working for it?
Question 3: Is it time-bounded?
A side quest has a natural end. You build the thing, you ship it, you come back. It is a contained excursion with a return ticket already in your pocket.
How long is the window?
Your permission slip
Permission Slip
Side quest approved, with a return ticket. Tell one person.
Main quest: not named yet
Side quest: not named yet
It makes: nothing named yet
The thread back: not said out loud yet
Window: not picked yet
Return by: no return ticket yet
- Question 1, generative: not answered yet
- Question 2, adjacent: not answered yet
- Question 3, time-bounded: not answered yet
Run the three questions.
Tell someone. Not for accountability in the traditional sense. The conversation itself might be the thing that gives you the permission, the way it did for Jess.
FAQ
What is a side quest, exactly?
A deliberate detour from the main project that refuels you without losing your momentum on it. Jess is specific about what it is not: not an escape hatch, not a reward you earn after finishing, and not a new direction. It is generative rest, which means you are still building, making, and moving, just in a different lane where the road is clear and the feedback comes faster. For a brain that carries a lot, a side quest sits next to focused work and makes it sustainable. The test is what happens when you come back. Jess came back to her five-hour intensive with more capacity than she left with. That is the difference between a side quest and a break that quietly costs you the week.
How is a side quest different from pushing through?
When you hit the wall, you are still capable, but the current path has gone dry. Jess uses the clinical language for this, executive dysfunction in a singular pathway: the brain is not broken and it is not checked out, the input to output ratio on that one path stopped working and it needs a different lane. Sustained effort on one project with no visible output or feedback makes the dopamine loop go quiet, and that is biology, not a character flaw. Pushing through with willpower forces output from a system that is asking for something different, and the harder you push, the more the system digs in. What the brain needs in that moment is a visible, completable win, something you can take from zero to done in a contained amount of time so the loop closes. A side quest provides exactly that win, in a lane where finishing is possible.
What counts as generative?
Something new exists when you are done that did not exist before. A draft, a tool, a framework written down, a conversation that produces a clear decision, an outreach message you actually sent. Something moved from your brain into the world in a form you can point to. The hard line Jess draws: a side quest makes something, avoidance consumes things. Researching is not automatically generative. Reading articles about the thing you want to build is not a side quest. Watching three hours of tutorials on a skill you might use someday is not a side quest. Those are consumption dressed up in the clothes of preparation, and your brain will absolutely try to convince you they are the same thing. If you cannot point to the thing, you are probably living in avoidance.
What does adjacent mean?
It lives inside the same ecosystem as your main quest, even if it is not the main quest itself. Jess calls it a side door in the same building: when you walk back in through the front door, you come back with a full tank. Her brand repository was adjacent because it serves the same audience she already serves, reflects the same values across everything she is working on, and connects directly to the larger body of work at Big Ideas Made Simple. Adjacent is not identical. There is a clear thread connecting the side quest back to the main thing, and the connection should be obvious the moment you say it out loud. If you have to work to explain it, it is probably not adjacent. This question also catches the detours that feel productive but are really new main quests in disguise. Three weeks into a side quest with a full business brand and a new identity means you did not take a side quest. You started over.
Why does it have to be time-bounded?
Because a side quest has a natural end. You build the thing, you ship it, you come back. It is not open-ended and it is not a new season. Jess pictures it as getting off a cruise ship knowing you have four hours on the tour and you have to be back before the ship leaves. The boundary matters because starting new things feels good. The dopamine hit at the beginning of a new project is real and significant, and high-capacity people get trapped chasing the hit that starting gives instead of the finishing that matters. A bounded scope with a return ticket already in your pocket is what separates a productive detour from a pattern of perpetual new beginnings. When you finish making the thing, the side quest is over, and the main quest is sitting there waiting, ready to be picked back up.
What if I cannot think of a side quest?
Use the tool Julia built for exactly this moment. Mission Detour takes your current main quest and a little detail about yourself and generates side quests that match who you are, what you are building, and your capacity, so when your brain is screaming for something different you are not staring into the void trying to invent one. It is free to start at missiondetour.com. And then tell someone. Not because you need accountability in the traditional sense, but because the conversation itself might be the thing that gives you the permission. That is what happened for Jess. A group chat with Julia and Trish unlocked a repository that had been sitting in screenshots on her camera roll. Your people do not just cheer for you. The right ones hand you permission you might not even know you need.
Go deeper
In Episode 21, Jess starts at the wall: a five-hour intensive for I Love Coaching, all the curriculum and the workbook, planned and ready, and an engine running with nothing left to give. The group chat with Julia and Trish did something she was not looking for. It gave her permission, not to stop working, but to work differently for a couple of hours. She built the personal brand repository, 49 tabs with AI prompts for every major piece of a brand or business, designed so she or anyone else could hand one tab to an AI tool or a team member and that tool or person would immediately know everything needed about that area of the business. Julia took the same conversation and built something completely different: Mission Detour, an app that generates side quests matched to your main quest and your capacity. Jess came back to the intensive with more energy, a clearer head, and enthusiasm she had worried she would not have 24 hours earlier. The episode then slows down for the framework: the dopamine loop going quiet under sustained single-path effort, generative rest versus passive avoidance, and the three questions walked one at a time, with the warning that your brain will try to convince you a side quest and avoidance are the same thing. They are not, and the difference matters because one refuels you and the other just delays the drain.
Listen to Ep 21: The Side Quest Is The Strategy (Give Yourself Permission to Detour)
Book referenced: Rest by Alex Soojung-Kim Pang (Jess names it with full transparency: it was sitting at the top of her to-be-read list, not finished, because the central argument landed before she read the whole thing. Serious sustained output requires deliberate rest built into the strategy as a non-negotiable, not a treat earned after finishing.)
Julia's tool: Mission Detour, free to start. Jess's side quest, free to grab: the Personal Brand Repository.
"Your people do not just cheer for you. The right ones hand you permission that you might not even know you need."
Related
- Episode 28: You're Not Behind (You're Just Waiting for Permission) Permission only comes from other people, and you have to go ask. The one-word test that tells stalling from a real season, and the conversation that breaks the permission cycle.
- Episode 29: Rest Isn't Stillness (What High Capacity Brains Actually Need) Rest and stillness are not the same thing. The two-pile audit for figuring out whether your rest problem is really a definition problem, and what actually refills you.
- Episode 23: The Idea You Keep Pushing Away? It's Trying to Tell You Something If the detour keeps showing up across unrelated contexts, it might not be a distraction at all. Three questions for telling a direction from noise.
Big Ideas Made Simple is a weekly podcast for entrepreneurs and fast thinkers building a business around who they are and how they operate. Hosted by Jess Webber. New episodes Mondays at bigideasmadesimple.captivate.fm.
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