How to Plan for The Seasons in Your Business in 2 Minutes or Less

Do you have a case of “business amnesia”?

Even if you’ve never heard that expression before (because I just made it up), I’m sure you can conjure up an image… 

…year after year, you KNOW there’s a better way to respond. But you keep making the same mistakes or defaulting to the same old bad habits. 

When you ignore the unique seasons in your business it’s like…

→  forgetting that you’ll need a winter coat in January 

→ or that your A/C bill will skyrocket in the heat of July

Sounds pretty obvious, but when it comes to seasons in business, too many entrepreneurs are blind to seasonal rhythms.

We’ve all been there. And while I can’t promise you’ll never make another mistake again, I can promise you that paying attention to the seasons in your workflow can keep you from getting into a toxic relationship with your business. 

>>Okay, Erin. So, what are the seasons of MY business?<<

Unfortunately, there is no one-size-fits-all road map when it comes to the seasons of your business. That’s because each business is one-of-a-kind and will have different seasons. 

These seasons will depend on your… 

  • business type
  • niche
  • ideal customer
  • offers & products
  • & business model

As a result, it is up to YOU as the CEO to identify your seasons, learn how to navigate them, and use this insight to plan ahead with strategy.

The good news: it doesn’t have to be a heavy lift! 

In just 2 minutes each week, you can start tracking the unique seasons and patterns of YOUR business to find more alignment and flow. 

PSST! Stick around ‘til the end (or scroll your way down there now) and I’ll give you my exact 2-minute journaling prompts to help you start tracking and planning for the seasons of your business right away.  

What are seasons in business?

Seasons in business are the recurring patterns and trends that occur in your work throughout the year. Most seasons fit into two categories: rest & hustle.

Seasons in business can be as simple as… 

→ the hustle of the holiday season that many product-based business experience.

→ the summertime slump lots of service-based businesses encounter.

→ the seasons you CHOOSE (such as vacation time) that align with your goals and values.

Some seasons will be obvious, while others are more subtle. They may even seem inexplicable! The beauty of seasons is that when you notice them, you can work with the external factors outside of your control and allow yourself the opportunity to influence internal factors so you can build in the seasons you value and need.

What Influences The Seasons in Business?

Some seasons happen naturally. They are a result of things out of your control (called external factors). Others depend on your specific business. You can shape these seasons to fit your needs, goals, and values (internal factors).

External factors include things like… 

  • the buying cycle 
  • the actual calendar seasons that impact your audience (think… Holidays, back-to-school season etc.)
  • niche-specific patterns 

Internal factors include things like… 

  • your capacity and availability
  • your work/life balance and needs (hello, kids’ schedules!)
  • or your specific offers

When you pay attention to the seasons in your business, you can learn to work in harmony with times of rest and hustle

Instead of feeling like a victim of circumstances, you can work with all the factors that impact your business throughout the year. With this knowledge, you can weigh your options and define your goals to decide how you’ll approach each specific season.

Why You Should Plan for The Seasons of Your Business

When you track and observe the seasons of rest and hustle, you can approach your business with fresh eyes. 

It’s an opportunity to take a step back and do some big-picture planning. Planning for the seasons of business allows you to be proactive and bust through unhealthy patterns instead of reacting poorly to the same challenges over and over again. 

The main reason to plan for these seasons is so that you can set yourself up for success during your busy seasons and be intentional with your time during your restful seasons. It’s a key part of running an effective, efficient, and scalable business. When you are in tune with your business seasons, you’ll be able to find flow and harmony with the internal and external factors that influence it. 

The Seasons of Rest and Hustle

Let’s explore what the seasons of rest and hustle look like and how you can leverage each of them rather than fight against them!

Seasons of Rest

Many businesses fail to leverage the seasons of rest and quiet. Too often we find ourselves sitting around, scratching our heads, wondering where everyone’s gone. Or we miss opportunities to give ourselves a TRUE break! Planning for seasons of rest can benefit your work in several ways. You may use seasons of rest throughout the year to fit your business needs and goals. 

Creative Ways to work with your seasons of rest:

  • Boost Sales. If you notice a slow trend in business, you may focus on ways to boost sales and income. This could be an opportunity for you to create promotions or incentives that will pull your business out of a recurring seasonal slump.

  • Maintenance. This is a time when you maintain your workload and work behind the scenes to keep everything running smoothly. Instead of pushing for growth, you can take advantage of seasons of rest in your business to shore up your foundation and update systems. You can also use this time to either prepare for future growth or anticipate your next big push. Lastly, it can be a good time to  “let the dust settle” and recover after coming off of a big launch or busy season.

  • Time OFF. Maybe you decide to use this time to go on vacation! If you notice a trend of things naturally quieting in your business, this could be the perfect time to unplug, no strings attached!  

  • Vision Casting. Another option is one of my favorites! I love to use seasons of rest for CEO Time. During this time, you can step away from the day-to-day of working IN your business to work ON your business! You can do this independently or with your team members. Taking CEO time helps you stay in tune with your big picture goals so that the smaller day-to-day actions of your work feel aligned with your values and mission.

The effort and planning you do during these seasons of rest will help guide and support you through the busier times of hustle.

COO Tip: Businesses will focus on some or all of these options during seasons of rest throughout the year. I highly encourage you to make choices based on your personal and business goals

Seasons of Hustle

When you plan for the seasons of your business you’ll be able to prep for the busy seasons with a roadmap you can follow. In these seasons of hustle, you are in the thick of it and won’t have the time or energy to thoughtfully map out plans and systems to support your work. This is not typically the time to launch a brand new idea or revamp an entire system of your business. When you plan ahead for the hustle, you’ll allow yourself to work in flow. You’ll set yourself up for a busy season… without the last-minute second-guessing or panic-induced pivots!

Creative ways to work with your seasons of hustle:

  • Stop making the same mistakes. Pay careful attention to the seasons of hustle that tend to overwhelm you the most. Leverage seasons of rest to put a plan in place that will prevent this in the future. Remember: insanity is doing the same thing over and over and expecting different results. 

  • Build Ease. Trust and rely on the work you did during your seasons of rest. The strategies you put in place in planning mode (when you are calm) tend to be more sound and thorough.

  • Prioritize Your Time. Pour your time, energy, and attention into following the plan and serving your clients. Your “Hustle Persona” will thank your “Rest Persona”. Often simply knowing that you will have the opportunity to reflect and refine later can make all the difference! Lean on your seasons of rest so you can take a load off and calm your concerns. 

  • Have a System. Take note of things you’d like to improve during your next season of rest. Instead of trying to fix everything in the middle of the chaos, stick to the plan, but have a system in place to make sure you return to it later when things calm down!

All “hustles” and “rests” are not created equal! 

It is important to acknowledge that the seasons of your business will ebb and flow. Some restful seasons will offer you the opportunity to plan and work behind the scenes while other seasons of rest will allow you to truly unplug. 

Likewise, some seasons of hustle will consist of developing new ideas and innovating for your business while other seasons of hustle will be all about client engagement and actively serving your customers. It is all a balance and part of the beautiful journey of entrepreneurship!

It’s also worth noting that seasons can vary in length. Some last for just a couple of weeks while others may last up to 6 months. As you observe the patterns that show up in your work, do so without expectation or judgement. 

How do I plan for the seasons of my unique business?

Understanding the seasons of your business can be a huge advantage to productivity, sustainability, and flow. As you now know, no two businesses have the same exact seasons. So the most important thing you can do right now is dive into the tracking process. 

The Tracking Process

Whether you realize it or not, your business has seasons that are cyclical. But you can’t know them unless you take the time to get to know them. Seasonal trends have to be tracked over time. Take time each week to write down reflections and you will be one step closer to getting in sync with seasonal patterns.

This can feel overwhelming at first. You might be asking yourself, how in the world am I supposed to document all of this for an entire year? 

Keep it simple and don’t overthink it. 

The goal is simply to have something you can easily refer back to and remember exactly what happened (because you have so much in your brain, you can’t expect yourself to remember the tiny details throughout the year). 

Your future self will thank your past self for keeping a running log of these patterns. As a result, you’ll find you can intentionally plan for incentives, launches, projects, and even things like time off, CEO time, and vacations (i.e. it may not be a great time to take some R&R at the height of your busy season). These are the kinds of decisions that seasonal trends will help you make.

Season-Tracking Journal Prompts

As your business guide, I’ve got you covered! This process can be simple and I’ve prepped the exact prompts you can use each week to help you successfully track your business seasons. It’s low lift and effective!

How to get started

First things first. Do you have 2 minutes to spare each week?

Yes?

GREAT!

>>As promised, let’s dig into the meat and potatoes of it all!<<

Here’s my tried and true method for tracking the seasons in your business.

Jot down a response to each of these prompts weekly. No need to write a novel, just start documenting and keep it simple. Get to the point so that your future self can easily observe trends, patterns, and events.

Journal Prompts:

  1. Here are the big projects or initiatives I was working on:

  2. This is what my capacity was:

  3. Here are external factors that had an impact on my time or business (i.e. holidays or buying patterns of your audience):

  4. Am I in a season of Hustle or Rest?

  5. On a scale of 1-10 How busy am I right now?

Tracking Tips:

  1. Keep these prompts somewhere easy to access. Create and bookmark a spreadsheet or jot your notes down in a small designated notebook. 

  2. Set a two-minute timer. Don’t allow this to become a huge task that eats up your precious time. Keep it simple and then move on!

  3. Set a weekly calendar reminder to help you stay consistent. I highly encourage you to make it part of your planning or weekly wrap-up routine.

  4. New habits can be tricky, so try to pair this new habit with something you love to do or already have established as a habit. Learn more about Habit Stacking here!

  5. Set a quarterly calendar reminder to review your notes. Choose 1-3 action items you can take next cycle to improve or enhance that season in your business. 

  6. Review your season-tracking annually.  Add this piece to your year-end review or big-picture business planning.

As you spend more time in your business and look back you can pay attention to when certain things hit, when you were busiest, when things were quieter, and which factors influenced those trends in your business. This will help you make future projections and plan more accurately and proactively. 

The Planning Process

The tracking process takes time. You won’t have an honest view of these seasons until the full year has passed. Even then, the longer you are in business, the more you’ll learn and realize about your distinctive patterns and workflows. As you get more familiar with your seasons, you can choose to move with them or counter the trends to fit your needs.

But that doesn’t mean you can’t start planning NOW. Each quarter, you should take some time to reflect on the tracking you’ve done over the past few weeks. As you gradually get to know the seasons of your business, you can put plans in place to support and leverage these different times. 

Take Action

Once you have enough data you can start to take action. 

Maybe your goal is to take a step back in the summer months for some intentional rest. With this goal in mind, you can carve out time in late winter & spring to create passive income products. Similarly, if the hectic holiday season no longer feels sustainable, you can block off time to prep for your holiday sales in July & August.

Big picture planning with the seasons will make your work easier and more impactful. You’ll feel empowered to create the life and business you envisioned when you started.

COO Tip: Big-picture seasonal planning won’t happen overnight! The more consistently you track your business seasons and the longer you’re in business the easier it will be to observe and respond. Year after year you’ll continue to take note of what’s going on in your business and gain new insight as you go.

Let’s Sum it Up

If you keep hitting the same wall in your business year after year… you need to track your seasons.

If you keep looking back and wishing you’d used that time DIFFERENTLY… you need to track your seasons.

If you want to stop reacting to one fire after another…you need to track your seasons.

Paying attention to the seasons of your business is profoundly impactful AND it doesn’t have to be hard. 

You now have the tools you need to track what’s going on in your business, stay on the pulse, and observe trends. Taking this time will help you see your work from a bird’s eye view. You can make intentional choices and implement strategic plans. When you work with the seasons of your business you can stop making the same mistakes over and over again. History repeats itself. But if you choose to learn from the past, pivot, and make new choices your business can continue to grow, flourish, and thrive. 


Planning for the seasons in your business can feel like uncharted territory. If you need a guide to lead the way, I’m here to support you as a 1:1 coach or outsourced COO. Schedule a free strategy session to map out your seasonal tracking plan today!

  1. […] When I allowed myself to get creative, I found ways to give back through things like small but heartfelt donations or hosting free workshops to communities I care about. I give when I can and how I can through each phase and season of my business.  […]

  2. […] ratio of time you spend working on your business or in your business will fluctuate from one season to the next. Nonetheless, this is a solid place to start when estimating how to work towards your profit […]

Let's Connect!
Follow Me  @erincantwellco