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How I'm Making the Most of Off-Season with Family Time and New Business Ventures

Writer's picture: Jennifer MilanoJennifer Milano

The most-asked question I get? 'What do you do during the off-season?'—Honestly, I just sit around waiting for limes to ripen. Kidding of course.


As the busy season winds down, I find myself with extra time to focus on the important things in life that often get overlooked. Family time has taken priority, and I’m thrilled to savor these moments together. Recently, we enjoyed a memorable trip to our cabin in New Hampshire, which sparked both adventure and quality bonding time.


We stumbled upon a local pond that turned into our very own playground for a family skating day. Surprisingly, I was able to keep up with my kids on the ice! Their laughter filled the chilly air as I glided alongside them. The joy we shared was truly infectious!


Wide angle view of frozen pond with skaters
Family skating on a frozen pond

Family outings like these are invaluable, especially during the off-season when we take a break from the daily grind. For entrepreneurs like me, the off-season can be tough. The drive to stay productive never completely disappears. Even as I relish quality moments with my family, my entrepreneurial mind is always searching for ways to fill in the gaps. Connecting with others who are navigating the same challenges has become a source of comfort and inspiration.


As I prepare for our next weekend adventure to Massachusetts to visit my husband's family, I reflect on how these gatherings can recharge our spirits. These trips not only create treasured memories but also help us gain fresh perspectives. The drive is often filled with laughter and excitement, reminding us of the joy family brings, even amid our busy lives.


In recent weeks, I have channeled my energy into launching a new venture that reflects my passion for helping others. I am excited to share that I've created a social media workshop tailored for entrepreneurs looking to thrive in 2025. This workshop will provide participants with valuable insights and actionable strategies to set their businesses up for success in the coming year.


Eye-level view of a mobile bar with drinks
Celebrating off season in style

This new venture aligns perfectly with my off-season reflections. It serves as a platform for growth and community connection. Knowing that I can support others while pursuing my goals brings me a deep sense of fulfillment.


Attending workshops allows entrepreneurs to unite, sharing our challenges and successes. I’ve had the privilege of connecting with a diverse group of innovators, all tackling the challenge of keeping their business ideas vibrant during quieter periods. Our discussions often cover how to maintain momentum when external factors slow us down. It reassures me to know I am not alone in this journey; together we navigate new paths to success.


Finding balance during the off-season can be tricky. There are times when the desire to achieve clashes with the need for relaxation and enjoyment. It's important to honor both sides. Giving myself the space to enjoy family time enriches my creativity and fuels my motivation.


Taking walks around the cabin, discovering local spots, or hiking nearby trails has offered me a wealth of inspiration. Nature has a special way of rejuvenating our thoughts, especially when we receive a break from screens and hectic schedules.


High angle view of a scenic New Hampshire landscape
Scenic view of the New Hampshire landscape

Looking ahead, I am eager to continue balancing family moments with my new business pursuits. The thrill of launching my social media workshop energizes me. Despite this excitement, I remain committed to nurturing my family relationships as a top priority and allowing my team to thrive behind the bar shaking up new and powerful cocktails.


For fellow entrepreneurs facing similar challenges, I encourage you to carve out time for your loved ones, even during busy seasons. Embrace small adventures, share laughter, and lay the groundwork for cherished memories. Investing in your personal and professional growth will lead to more satisfying experiences at home and in your work.


As I contemplate this chapter of our journey, I feel immense gratitude for what lies ahead, for the family time we've cherished, and for the growth that awaits us in the coming months. The off-season may present challenges, but it is also an opportunity to reflect, connect deeply, and prepare for what’s next. Here’s to family, new adventures, and achieving success together!



In summary, making the most of the off-season is about nurturing those meaningful connections with family while pursuing vibrant goals. Our experiences shape our paths, and as I step into this new venture, I am excited to embrace what the future holds. Stay tuned for some exciting changes coming your way!


Checkout my new adventure on Social Media Marketing: Crafted Content Club


Cheers,

Jen

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