In a candid conversation, Jeremy Axel and Douglas Cox unveil the unvarnished reality of entrepreneurship during the holidays, sharing hard-won insights and actionable strategies for those who remain "always on" while the world around them pauses.
In this in-depth blog post, we’ll break down the main themes and actionable tips from their discussion, providing a comprehensive guide for entrepreneurs seeking to navigate the holiday season with intention, balance, and well-being.
The Unseen Pressures of Holiday Entrepreneurship
While the holidays are a time for most to unplug, entrepreneurs often find themselves hunched over laptops, racing to meet deadlines and respond to customer demands. The pressure to be “always on” is compounded by:
- Cultural expectations of work-life balance rarely match entrepreneurial reality.
- Self-imposed urgency — the fear of missing out on opportunities if not immediately responsive.
- Provider guilt — the emotional weight of ensuring family needs are met, often at one's own personal expense.
- Loneliness and isolation — the sense that no one else fully understands the unique burdens of leadership.
Jeremy Axel and Douglas Cox's conversation highlights that these challenges are not just seasonal but are magnified during the holidays when societal expectations and family dynamics come to the forefront.
Tip 1: Redefine Work-Life Balance
Key Insight: Balance is not about equal time, but about harmonious flow and intentional prioritization.
In-Depth Strategies:
- Ditch the Myth of Perfect Balance:
- The idea that you can give equal energy to work and family at all times is unrealistic. Instead, recognize that different seasons require different priorities. Sometimes work will demand more; other times, family will.
- Embrace Flexibility:
- Allow yourself to shift focus as needed. For example, if a critical business deadline falls during the holidays, communicate openly with your family about your temporary focus, and plan dedicated family time afterward.
- Set Realistic Expectations:
- Avoid disappointment by acknowledging that “balance” is dynamic. As Douglas Cox notes, “Every season of life demands different priorities.”
Actionable Advice:
Regularly assess your current season and adjust your expectations and commitments accordingly. Use weekly check-ins with yourself (or a partner) to recalibrate.
Tip 2: Set and Maintain Boundaries
Key Insight: Boundaries are essential for protecting your time, energy, and mental health, especially during the holidays.
In-Depth Strategies:
- Communicate Boundaries Early:
- Let clients, customers, and team members know your holiday availability in advance. Set up auto-responders or clear “out of office” messages.
- Enforce Technology Limits:
- Designate specific times to check emails or respond to messages. As Doug jokes, “Ignore texts on Christmas Day”, and mean it.
- Involve Your Family:
- Share your boundaries with your family so they can help hold you accountable and understand your commitments.
Actionable Advice:
Create a “holiday work schedule” and stick to it. Use tools like calendar blocking and do-not-disturb modes to reinforce your boundaries.
Tip 3: Prioritize Presence Over Perfection
Key Insight: The most meaningful moments are often the simplest, being present with loved ones, even when tired or distracted.
In-Depth Strategies:
- Value Small Moments:
- Doug’s story about decorating cookies with his kids, despite exhaustion, underscores that these are the memories that last.
- Let Go of Guilt:
- It’s normal to feel torn between work and family. Acknowledge the feeling, but don’t let it rob you of joy in the present.
- Practice Mindful Transitions:
- Before shifting from work to family time, take a few deep breaths or a short walk to reset your mindset.
Actionable Advice:
Schedule “micro-moments” of presence, 10-15 minutes of undistracted time with family, even on busy days. These add up and matter more than grand gestures.
Tip 4: Recognize and Address Entrepreneurial Loneliness
Key Insight: The provider role can be isolating, especially when you feel responsible for everyone’s well-being.
In-Depth Strategies:
- Acknowledge the Emotional Weight:
- Jeremy’s admission of eating cereal while his kids have something else is a metaphor for self-neglect. Recognize when you’re putting yourself last.
- Share Your Experience:
- Talk openly with trusted friends, mentors, or other entrepreneurs about your struggles. You’re not alone, even if it feels that way.
- Seek Professional Support:
- If feelings of isolation or overwhelm persist, consider speaking with a coach or therapist.
Actionable Advice:
Join a mastermind group or local entrepreneur network for regular connection and support.
Tip 5: Build and Lean on Your Support System
Key Insight: Accountability partners, whether spouses, friends, or colleagues, are crucial for staying grounded.
In-Depth Strategies:
- Invite Feedback:
- Encourage your partner or family to let you know when you’re overextending or neglecting self-care.
- Share Responsibilities:
- Don’t be afraid to delegate or ask for help, both at work and at home.
- Express Gratitude:
- Regularly thank those who support you, especially during high-stress periods.
Actionable Advice:
Schedule regular check-ins with your support system to discuss challenges and celebrate wins.
Tip 6: Embrace Rest as a Strategic Asset
Key Insight: Rest is not a weakness, it’s a necessity for long-term effectiveness and well-being.
In-Depth Strategies:
- Reframe Rest:
- View downtime as an investment in your business and family, not as lost productivity.
- Schedule Breaks:
- Block out time for rest and treat it as non-negotiable. This could be a full day off, a few hours for a hobby, or simply a nap.
- Monitor Burnout Signs:
- Watch for irritability, fatigue, or declining performance, these are signals to slow down.
Actionable Advice:
Plan at least one full day during the holidays where you are completely unplugged from work.
Tip 7: Accept Imperfection and Redefine Traditions
Key Insight: The “perfect” holiday is a myth. Embrace what works for your unique family and business situation.
In-Depth Strategies:
- Let Go of Comparison:
- Social media and cultural narratives can create unrealistic expectations. Focus on what brings your family joy, not what others are doing.
- Redefine Traditions:
- If a big family dinner isn’t possible, create new rituals—movie nights, game sessions, or simple walks together.
- Communicate Openly:
- Discuss holiday plans and expectations with your family to avoid misunderstandings and disappointment.
Actionable Advice:
Ask each family member what one thing would make the holidays special for them, and prioritize those moments.
Final Thoughts: Intentionality and Self-Compassion
Jeremy Axel and Douglas Cox’s conversation is a powerful reminder that entrepreneurship during the holidays is a complex, emotional journey. The key to navigating it successfully lies in intentionality, setting boundaries, prioritizing presence, and embracing imperfection. Most importantly, practice self-compassion. There is no perfect formula, and it’s okay to stumble as you find your own path.
Remember:
- You are not alone in these struggles.
- Small moments of presence matter more than grand gestures.
- Rest and support are not luxuries; they are necessities.
Wishing you a balanced, meaningful, and restorative holiday season.
You can watch “The Holiday Grind: The Lonely Reality of Being the Boss in Q4” on YouTube and as always, the audio version streams free on Apple Podcasts, Amazon Music, and Spotify.
