Lessons from a Messy Day

Let’s get real for a second: I’m struggling.

After 21 years in business, you’d think I’d have everything under control. And on some days, I really do. But then there are days like today, when I feel like I’m completely falling apart.

Here’s the thing: I’ve been inconsistent with my Thriv content. And it’s been eating at me. I feel like I’m failing—like I can’t pull it together enough to give the parts of me that I want to give to nurture this community.

And then there’s the spiral:

  • I waffle about the direction I want to go with my knowledge and experience.

  • I feel the need for a team I can’t yet afford.

  • I wrestle with making money and the idea that not many people might be reading or responding to my work.

And the butt-biter? Sometimes I feel like I’m not needed.

There—I said it. Out loud.

I know that might sound strange coming from someone who’s been in business for over two decades. But in full transparency, these feelings are real, and they sneak in when I least expect them.

Here’s what’s keeping me grounded: I know what I’d tell YOU if you were sitting in front of me, pouring your heart out about feeling this way.

I’d look you in the eye and say:

Your gift is a big deal. You are a big deal. And the work you’re doing matters.

So today, I’m taking my own advice. I’m going back to what I teach my clients—starting at the beginning.

When my clients are struggling, as team leaders and company owners, the first thing we do is revisit the foundation:

  • Reconnect with your accomplishments.

  • Realign with your value.

  • Tap back into your purpose.

So, I’m doing the same. I’m not going to let this struggle define me. Instead, I’m using it as a reminder that growth isn’t always pretty, and leadership isn’t about having it all together all the time, and whatever you do don’t give up

Some days, we lead. Some days, we’re the student.

Today, I’m the student.

To anyone out there who’s also feeling like they’re falling apart—like they’re failing despite their best efforts—I want to remind you: it’s okay.

We’re human. The messy moments are part of the success.

Feeling unmotivated to keep you or your team aligned with goals?

It’s a common challenge for leaders, especially when you’re juggling multiple ideas and responsibilities—but it’s solvable with strategy and intention. Here’s how to realign your focus, inspire your team, and create a rhythm that works for everyone.

1. Reconnect with Your "Why"

Revisit the core purpose of your team’s goals. Is it to drive innovation? Build trust within the organization? Achieve specific milestones? Write down your “why” and share it with the team—it’s the guiding light that fuels motivation and keeps everyone aligned.

2. Streamline Team Processes

Simplify goal management with systems that boost efficiency:

  • Batch Tasks: Dedicate specific times for brainstorming, planning, and execution. For example, brainstorm strategies on Monday, assign tasks on Tuesday, and review progress on Friday.

  • Define Priorities: Clarify the top 3-5 focus areas and use these as the foundation for all initiatives.

  • Use Templates: Create reusable templates or standard operating procedures for reports, meetings, or communications to save time and maintain consistency.

3. Set Realistic Goals

Consistency isn’t about overloading you or the team. Set achievable milestones and create a manageable pace. Whether it’s one project update per week or quarterly check-ins, focus on what’s realistic to avoid burnout.

4. Focus on Impact Over Volume

If the you or the team feels stuck in busywork, shift the focus to tasks that make the most significant impact. Encourage quality over quantity in every initiative to ensure meaningful progress.

5. Leverage Collaborative Conversations

Team meetings and brainstorming sessions are goldmines for actionable ideas. For example:

  • Turn discussions into project roadmaps or content for internal updates.

  • Use feedback from the team to refine goals and align strategies.

  • Share meeting highlights as updates to keep everyone on the same page.

  • Follow up on action steps to ensure everything is moving forward.

6. Lean on Strengths

Identify the strengths within yourself and your team and give them permission to shine:

  • Delegate tasks based on skills and enthusiasm.

  • Encourage team members to take ownership of initiatives they’re passionate about.

  • Celebrate diverse approaches to problem-solving—it fosters innovation and engagement.

7. Delegate or Automate Where Possible

If you’re feeling overwhelmed by logistics:

  • Delegate: Assign administrative tasks to trusted team members or assistants.

  • Automate: Use tools for task management, scheduling, or reporting to reduce repetitive work.

8. Foster Accountability and Feedback

Create a collaborative loop that keeps the team engaged:

  • Share goals and milestones openly with the team.

  • Encourage feedback on processes and strategies.

  • Commit to regular updates that reflect progress and adapt to input.

9. Celebrate Small Wins

Recognize even the smallest accomplishments, whether it’s meeting a deadline, solving a tricky problem, or receiving positive feedback. Acknowledging progress boosts morale and reinforces the team’s collective efforts.

10. Experiment and Innovate

Encourage the team to try new approaches without fear of failure:

  • Pilot a new project management tool.

  • Test unconventional solutions to recurring challenges.

  • Share experimental wins and lessons learned—it’s part of growth.

11. Remember: Progress Over Perfection

As a leader, remind the team (and yourself) that perfection isn’t the goal—progress is. Focus on authentic collaboration, incremental achievements, and staying aligned with your shared purpose.

Need support in aligning your team and processes? Let’s break down your goals into actionable steps and create a simple, effective plan to keep your team motivated and focused.

Join us for the “Elements to Finding your Flow” workshop. (recorded live November 25, 2024)

Jenn Ocken

Jenn Ocken is a creative powerhouse with a lens in one hand and a journal in the other. With over two decades of experience as a photographer, she’s not just capturing moments – she creates visual stories.

For Jenn yes it’s about the moments, but also turning chaos into clarity. With her keen problem-solving skills armed with a graphic arts management degree, she ventured into the world of business early on. Her blend of creativity and entrepreneurial spirit soon had her thriving as a professional photographer, even though she never formally studied photography. Talk about unconventional success!

https://www.jennocken.com
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