Mindful Planning: How I Use The Seasons To Set Goals and Track Milestones

For too long, even after starting my own business, I tried to hack my work style to fit into the "typical" routine - diving into difficult projects by 8 a.m. every Monday, taking meetings anytime, any day, and pretending I was ready to "hit the ground running" with fresh ideas and new perspective come January 1st (holiday emotional hangover be damned).

I did this because I assumed it was the only way. I thought that in order to be successful, I had to consistently deliver at high speed - all-out energy, all of the time. When things didn’t work, and when I continued to feel worn down and exhausted, I assumed something was wrong with me. I thought I just didn’t have what it takes - that maybe I wasn’t fit for this entrepreneur life. Because if you’re not responding to emails and finalizing presentations at 11 p.m., can you even call yourself an entrepreneur?

I was tired and confused. I was resentful. I felt guilty for shutting down my laptop at 4 p.m. to go pick-up my daughter from school. I constantly felt like I had too much to do and not enough time to do it all. I was often unkind to myself and short with the ones I loved. So, I took a deep dive into the topic of efficiency.

All I need to do in order to feel better is change the way I organize my to-do list!” and when that didn’t work, “I need to just do calendar-blocking! I’ll be able to get more done! Then I’ll feel better!” And then, finally, “OK. What I need to do is just wake up three hours earlier so that I can have a morning routine, answer emails, get my daughter ready for school and then jump into my to-do list.”

Long story short - none of it worked.

The best change I’ve made in my personal and professional life is embracing the slow hustle. Since embarking on that new journey, I’ve learned a lot about seasonal working and living, and this, by far, has had the biggest impact on my business mindset and productivity. Seasonal living and working isn’t just about slowing down - it’s about becoming more mindful of your body’s natural rhythms in order to maximize output in a way that leverages (and protects) your energy levels (and sanity). And I don’t mean “energy levels” in the “woo-woo” sense - I mean it in the physiological sense.

Working in-tune with the seasons naturally builds in time for work and rest.

Now, I chart my daily, weekly and annual business roadmap using my intrinsic productivity as a guide, not an arbitrary calendar dictated by Corporate America. And, I've noticed the quality and efficiency of my work improve drastically. Using the seasons to guide my business also makes me more organized because I have a natural model for when to focus on certain tasks.

Before I dive into how I conduct annual planning for my business, I do want to make a point in saying: This new way of work and life required some serious reprioritization on my part. I had to recognize that it might take me longer to accomplish certain goals, to tackle certain milestones. I had to make certain sacrifices. But this is a conscious decision I made in order to live a mindful and present life that felt more...balanced, or blended, at a time when I needed it most.

I recognize that this philosophy isn’t for everyone - either because your personality is different than mine or because my life circumstances are different and, I recognize, privileged. So please, take this all with a grain of salt - it might not be doable for you, but maybe there’s something you can take away from it.

Inspired by nature, this is how I use the seasons to create a sustainable yearly workflow that's allowed for better career-life blend. I'm no expert - and, trust me, I was a skeptic at first - but the improvements to my mindset are too good not to share.

There’s A Reason For Each Season

Our bodies are built to naturally react in certain ways to certain seasons. The sun, the weather, the length of days - they all have an affect on us. I use the seasons for annual planning. Here’s what I’ve learned each season is good for (I broke winter into two sections, you’ll see why):

Early Winter

It’s the darkest time of year, perfect for resting and recharging, and reflecting on what worked well in your business this year and what needs to be improved upon in the coming one. Embrace the stillness of winter by dreaming up your next big goals, knowing there will be plenty of time to set “resolutions” later on.

You don’t need to do it all before December 31st. Wrap up this year - don’t focus on the next one just yet. Spend time with loved ones and those closest to you. Dream up new dreams, but don’t feel the pressure to make them “official” yet. For me, this is when ideas are swirling around in my head and sometimes scribbled down into a notebook - but nothing is made official yet.

Late Winter

The days are getting visibly longer and, depending on where you live, there are new signs of life out in the world. We begin to wake-up after a restful period and are likely bursting with new ideas. Set goals or intentions, or resolutions, if that’s what you call them, and start mapping out a rough draft of a plan for reaching those goals. Start the work and refine what needs to be changed on the back end, so that you’re well-equipped to dive into the new initiatives come spring.

A quick note here - I no longer set “resolutions” until well after January 1. Typically, I visit these ideas after I’ve returned to work for at least two weeks after the holiday season. This has really allowed me to soak in the holiday vibes and then slowly ease back into the “real world.”


Rebirth and planting! Get rid of any clients, projects or processes that no longer serve you (i.e. spring cleaning). It’s time to start giving life to the ideas that were brewing in winter. Finalize your plan. Set milestones. Check in on your goals, reach out to the people you need to reach out to. Start doing the actual work and marking off those to-do’s. Spring is a great time to launch new products or programs. Get out there!


It’s all about growth and abundance. Summer is very much about outward-focused energy - continue to work hard on your business and you’ll have a nice harvest to look forward to come fall. Do big things now. It’s a meaningful time to make major progress on your goals.

If you launched a new initiative in the spring, summer is a good time to nurture and refine. It’s also a good time for play - hello, summer vacation. Especially here in Phoenix, the days are blazing and I’m worn out by 2 p.m. So, my work schedule shifts a bit in the summer. When I’m at work, I’m extremely focused and checking off tasks. When I’m done for the day, I’m extremely done for the day.


Harvest, gratitude, death (i.e. letting go). Early fall is another great time to launch new products or projects, because we’re back in a work mindset after late-summer play. But by late fall, the nights are longer than the days again and our energy levels are beginning to drop in certain ways. It’s time to take stock of what you’ve accomplished this year. Celebrate your wins. What are you “harvesting” from your hard work this year? Like spring cleaning, late fall (Thanksgiving-ish and on) is a good time to get go of whatever is no longer serving you - clients, projects, systems, programs, subscriptions, etc.

Come fall, I’m almost 100 percent in harvesting mode. In my business, that looks like nurturing my existing client relationships and projects, revisiting milestones to see what needs to be done before December, and making handwritten edits on all of my plans for ideas on what to change come the New Year. And, just to drive the point home, the time between fall and late winter is all about giving these lessons and their subsequent new ideas room to breathe before you pick it all back up again come January.

I did not come up with this philosophy on my own. Here are some of my favorite resources for seasonal living:

Being Boss Podcast: Living Seasonally

The Seasonal Soul: Wheel of the Year Workbook

The Cosmic Calling Podcast: Living & Working Seasonally with Emily Thompson

In my next blog post, I’ll share how I use the moon phases and astrology to plan out my monthly and weekly schedules. In the meantime, what kind of questions can I answer for you about seasonal planning? Drop one in the comments below and I’ll do my best to help!


Katarina is the owner of Redefined Communications, and founder and editor of RUBY Media. She is a girl’s girl, traveler, wife and mama trying her best to navigate this crazy world with a little bit of grit, and a whole lot of humor and grace. Follow her on Instagram.