Personal systems take time

One of the most common issues I see in management, especially with early-career employees, is a struggle to stay organized and manage time well.

I have empathy for it because I was the same way. In college and my early career, I bounced between to-do apps, note-taking systems, project management tools, paper journals, and weekly planning templates. It wasn’t until my late 20s that I landed on a system that not only worked, but that I could actually stick to.

Personal systems take time to develop. And they should be deeply personal. You can’t just adopt someone else’s setup and expect it to work without modification. Everyone’s wired differently. What clicks for me might drive you crazy – and vice versa.

When we talk about personal systems, we often think of task lists and calendars. But it’s broader than that:

  • Macro tracking for fitness or nutrition
  • Personal reviews and reflections
  • Goal tracking
  • Morning routines or end-of-day resets

All of these systems help us stay on track, but ask anyone who uses one and they’ll tell you they are tough to master. Good systems take time to create and refine, and they should make your life easier, not harder. If you’re constantly fighting to maintain it, it’s the wrong one.

If you’re still figuring it out, be patient. Experiment, reflect, and adjust as needed. The goal isn’t to get it perfect; it’s to get something that helps you show up for yourself and others consistently.

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  • The (dreaded) weekly report

    I remember in college when I was a state officer for DECA. We had to generate a fifth-of-the-month report (FOMR) for our coach outlining the projects, wins, and challenges we worked through that month.

    I hated them.

    Then I got into the professional world and had to do more reports – some internal, some client-facing.

    I still hated them.

    I get it – writing a report is a big lift. Whether it’s weekly, monthly, or quarterly, they not only can take a lot of time to complete but there is always the fear of leaving something out or getting called out for something you include.

    Despite their reputation, I am a big believer in weekly reports. They can be a powerful thing if done well. But most of the time they’re not. They become a formality or a Friday afternoon chore. A waste of time. The problem? No one ever explains why they’re important, or what a good one looks like. They should be seen as an opportunity to tell the story of the week.

    Here’s how I approach weekly reports as a manager:

    • They’re not a task list. They should tell the story of the week: progress, wins, challenges, and lessons learned. If it was a great week, the report should clearly communicate why. If it was a bad week… same thing.
    • Provide a guide: If you want to avoid reports being phoned in, set clear expectations for what reports should communicate. I literally created a “good report / bad report” side-by-side comparison for my team when I noticed a pattern of unhelpful reports, and it worked.
    • Good reports create better one-on-ones. The weekly report should be your pre-read for check-ins. That way, they can focus on coaching, providing context, working through challenges, and professional development – not just a project status that can be communicated another way.

    When done correctly, weekly reports help leaders stay connected to what’s really happening on the team and help employees feel seen, supported, and celebrated.

    Oh, by the way, managers: make sure you actually read them 😉

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  • 36 hours of pain

    There’s probably something big you’re avoiding right now.

    I’ve been there too: Staying in a job I no longer liked because starting a new one felt like a pain in the ass. Keeping a toxic employee around because I didn’t want to have the awkward 20-minute conversation to let them go. Waiting until the last minute to start a big project because I didn’t know how to get started.

    In Traction, Gino Wickman calls this the “36 hours of pain.” He tells the story of a manager who knew one of his longtime employees was no longer the right fit for the role as the company grew. The thought of letting them go was agonizing. But after the 36 hours leading up to the termination, once he finally did it, the work environment changed overnight. His team even thanked him for making the tough decision.

    We trade long-term peace for short-term comfort all the time. Over time, these constant tradeoffs deteriorate our motivation, mental state, confidence, and even our physical health.

    A tough moment today – a decision, a conversation, a confrontation with reality – can save you from months or years of frustration.

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  • The small moments matter

    That $5 donor can become one of your biggest donors.

    That new follower can become your future business partner.

    The shy intern may run the organization one day.

    I’ve been amazed in my career at what the small moments can turn into with some cultivation and patience.

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  • You’re not that unique

    Neither is your organization. I know that’s really hard to hear or accept.

    You’re not so unique that the basics of leadership, systems, and clarity don’t apply to you.

    You’re not so unique that you just happen to attract bad hires. Maybe you have weak management.

    You’re not so unique that setting clear goals, building a healthy culture, and creating clarity somehow aren’t “your thing.”

    Saying you’re unique is convenient. It’s a way to avoid change, sidestep responsibility, and ignore the hard truths every other leader eventually has to face.

    The good news is, you’re not alone. But you’re not exempt either.

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  • Gen Z Isn’t Cooked: Finding Purpose in an Age of Despair

    The biggest crisis facing young Americans today is a lack of purpose. They wander through life weighed down by hopelessness, convinced the future isn’t worth fighting for. They can’t afford basic necessities because of rising costs and stagnant wages. They’re told they’ll never have homes. Marriage and kids are, for many, out of the realm of possibilities. And to make it all worse, the climate doomers say they won’t have a future because climate change will suffocate us all.

    The emptiness many young people feel today is profound, and originates from multiple sources, but one especially stands out: climate doomerism, the belief humanity is on an unstoppable march toward destruction, has become a defining feature of our generation.

    The story told to millions of young people is the planet is dying, the system is rigged, and the future is lost. When that message becomes the moral framework for a generation, what hope is there?

  • Clarity comes from systems

    They say clarity is kindness, and I tend to agree. The clearer we are about vision, expectations, roles, deadlines, deliverables, etc., the better our teams become.

    I’ve learned that clarity doesn’t appear out of thin air. It’s an intentional commitment an organization makes to its people. And the way you create greater clarity, in my view, is through building better systems.

    Consider a few common sources of stress in an organization:

    • Unclear roles: When people don’t know what they own or what others own, you need a system that proactively defines roles and responsibilities.
    • Projects are vague: The deliverables and deadlines are fuzzy, so you likely need a better project kickoff and management system.
    • Poor communication: If key people aren’t “in the loop,” you might need an internal comms system that makes sure updates flow the right way at the right time.
    • Decision-making bottlenecks: If people don’t know who can make what decisions, you may lack a system for defining authority and approvals.
    • Mission drift and shiny objects: If your team struggles to stay aligned on long-term goals, or too many “exciting ideas” keep popping up, you need a system for setting plans and regularly reviewing goals.

    Again and again, when an organization lacks clarity, it’s not just a communication issue, it’s a systems issue.

    If you want to create greater clarity, try identifying the missing system.

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