TL;DR: Annual goal setting often fails entrepreneurs because businesses pivot too quickly. The six-week planning cycle offers a better alternative: choose 1-2 large projects and 4-8 smaller tasks every six weeks, execute for six weeks, then take two weeks to review and plan the next cycle. This system, popularized by Basecamp, keeps you focused while allowing flexibility to adapt to changing priorities throughout the year.
If you’re like most entrepreneurs, you’ve been instructed to create annual goals and then break them down into quarters.
And, if you’re like most entrepreneurs, this isn’t working for you AT ALL.
Why not?
Are you just terrible at keeping your promises to yourself?
Is there something wrong with you?
I’m not sure who’s reading this, so I can’t REALLY answer those questions for you (sorry), but I can tell you one thing: it’s not your fault if annual goal setting isn’t working for you.
It’s an outdated system that just doesn’t fit most entrepreneurial business.
I learned this the hard way in my business. Years ago, I created annual goals and then set up this fancy spreadsheet to break that down into quarters and then months.
But as my business pivoted and my priorities shifted, that plan became less and less relevant. All it managed to do is make me feel deeply behind on things that weren’t really even relevant anymore.
And I didn’t have any space to chase new, innovative ideas along the way.
Enter the six-week planning cycle. We’ve been using it for a few years now, and it’s the perfect fit for us.
Jason Fried of Basecamp introduced the world to this structure, and it’s now been adopted by a number of other businesses, including Intercom and Buffer.
Six weeks is a magical time period.
Long enough to keep shiny object syndrome at bay.
Short enough to let you adapt, learn, and pivot.
And it’s pretty simple! All you have to do is sit down, pick a few things you want to do over the next six weeks, post them somewhere you can see them, and then dive in. After six weeks has gone by, you get two weeks to decompress and plan until you start the next one, leading to six cycles over the course of one year.
I’m about to start a new six-week cycle, so I thought I’d give you a window into how this works at Smooth Operator (with steps you can follow too).
How Do You Set Up a Six-Week Planning Cycle?
Setting up your first six-week cycle starts with a brain dump of every project and task you’d like to accomplish in the near future. Skip ongoing client work or routine tasks like checking emails, but include those nagging projects that have been on your mind, like finally clearing out your inbox or redesigning your website.
Once you have everything written down, evaluate your list based on your availability, priorities, and yearly targets. Pick 1-2 larger projects and 4-8 smaller projects that you can realistically commit to over the next six weeks. Write this final list down and post it somewhere visible where you’ll see it regularly.
For overwhelming projects, break them down by week. A website redesign might look like: Week 1 for brand finalization, Week 2 for homepage copy, Week 3 for about page copy, Week 4 for remaining site copy, Week 5 for design phase, and Week 6 to begin review. This breakdown helps you track progress and set realistic expectations about what you’ll actually complete.
Why Does Six-Week Planning Work Better Than Annual Goals?
Six weeks hits the sweet spot between focus and flexibility. It’s long enough to make meaningful progress on substantial projects while keeping shiny object syndrome at bay, but short enough to let you adapt when your business pivots or priorities shift. Unlike annual planning that can become obsolete within months, six-week cycles keep your goals aligned with your current reality.
The magic really happens in how you handle new ideas. When you attend a webinar, read an inspiring post, or wake up at 4am with a brilliant idea, you simply write it down and add it to your running Ideas list (NOT your active to-do list). Then you get back to your current commitments. When it’s time to plan your next cycle, you can evaluate that idea objectively with just enough distance to know if it truly fits your goals.
This system also eliminates the guilt and overwhelm of falling behind on irrelevant goals. Instead of feeling like you’re constantly failing at your annual plan, you complete focused cycles and learn from each one, adjusting your approach every six weeks.
What Happens During the Two-Week Break Between Cycles?
The two-week break between six-week cycles is your time to decompress, reflect, and prepare. This buffer period prevents burnout and gives you space to think strategically about what comes next. You can pursue a fun side project, explore new ideas without pressure, or simply recharge.
Most importantly, this is when you review your previous cycle. Ask yourself what projects you finished and what outcomes they produced. Identify which projects drained your energy or created resistance, and explore why. For incomplete projects, determine whether you made a conscious, strategic choice based on changing priorities or whether procrastination got in the way. Finally, capture what you learned to apply to future cycles.
This reflection only takes a few minutes but makes you exponentially more strategic about picking your next set of projects. Then you rinse and repeat, starting the cycle fresh with clarity and energy.
Frequently Asked Questions
Q: How many six-week cycles are there in a year?
A: There are six complete cycles in a year. Each cycle consists of six weeks of focused work followed by two weeks for review and planning, totaling eight weeks per cycle. This structure (6 weeks + 2 weeks) × 6 cycles = 48 weeks, which means you’ll have a few ‘bonus weeks’ over the course of the year. I use these to catch up, which is very handy.
Q: What if I don’t finish all my projects in six weeks?
A: Not finishing everything is completely normal. During your two-week review period, evaluate why projects remained incomplete. If priorities shifted and you made a conscious choice to deprioritize something, that’s strategic decision-making, not failure. If procrastination was the issue, use that insight to adjust your next cycle. Unfinished projects can roll over to your next cycle if they’re still relevant, or you can let them go if priorities have changed. If you’re like me, you’ll probably get angsty about this, which is a great motivator for knocking it out so it doesn’t take up another project slot.
Q: Can I add new urgent projects during a six-week cycle?
A: The system is designed to help you stay focused, but true emergencies happen. If something genuinely urgent arises that can’t wait six weeks, address it. However, for most “urgent” ideas that pop up, write them down on your running project list and return to your committed projects. This practice helps you distinguish between genuine urgency and shiny object syndrome. You’ll be surprised how many “urgent” ideas no longer seem critical when you review them objectively during your next planning session. Letting the shine wear off a bit is useful.
Q: How does six-week planning work with a team?
A: Share your six-week priorities with your team at the start of each cycle so everyone knows what to focus on and can work in the same direction. Over time, you can delegate entire projects to team members, giving them ownership while you provide support. This clarity helps your team prioritize their work and reduces the constant question of “what should I be working on?” It also creates natural checkpoints every six weeks for team alignment and feedback.
Q: Do I need special tools or software for six-week planning?
A: No special tools are required. You can use a simple notebook, a digital document, a project management tool you already use, or even a whiteboard. The key is posting your 1-2 large projects and 4-8 smaller projects somewhere visible where you’ll see them regularly. I have a database for my ideas list, and then my sprint commitments get printed or written down (depending on my mood). Choose whatever system works best for you and your team.
