If you’re struggling at work…

I’m working with a new client who’s having trouble keeping his entrepreneurial work organized. He told me he has problems with his physical office space, and that he takes on too much work to have a private life.

I’m meeting with him next week and have been working on my notes. My first thoughts were around the space he’s in and the work he produces…

  • What’s on his desk?
  • What’s on his computer desktop?
  • How and what does he file?
  • Where is his work stuff stored – and is that in order?
  • If we clear off the desk, is there somewhere else to put things?
  • What does he do with trash/recycle to keep his space clear?
  • How does he communicate with clients? Verbally? With documents? Through emails or texts?
  • How are docs organized on his computer and physically on his desk?

Then we’ll talk about work habits – what a typical week looks like for start and end times, how tasks are prioritized, what his email and phone habits are, and how he keeps himself organized with a calendar, loose notes, a to-do list, etc.

As I pictured this, I felt like I was missing the mark. Now, rather than start with a focus on what feels like the answer to the question, I’m going to start instead with questions about how he feels about his work.

  • Describe a time where disorganization at work has messed you up.
  • How does lack of organization impact the rest of your life?
  • What would you like most to fix?
  • Describe organizational challenges throughout life. Are the current issues part of a normal trend? Or are they new?
  • Describe a typical process with a client – what are the problem areas, hitches, and slow downs?
  • Do you have repeat clients?
  • How do you like to present yourself to your clients? As an expert? Humble? Efficient? Laid back?
  • Is there any financial impact from your lack of organization?
  • What motivates you at work and at home? Making more money? Free time? Recognition?
  • What do you do with your free time?
  • What part of your work is high energy and what parts drain your energy?
  • What do you love to do and feel you are good at doing?
  • What do you like least about your work and feel you’re bad at doing?

When you’re trying to resolve work issues or any issues with organization, it’s tempting to start with your physical space. Just declutter and everything will be perfect! But then the clutters builds up again. Desks grow new piles. And a well-intentioned to-do list is set aside.

To get to a longer-term solution, it helps to get to the emotional side of what you do: How do you feel about the work you’re doing?

The goal is to get organized and STAY organized. Don’t waste time!

We went on the annual Garden Tour in Cape Elizabeth, ME on Saturday which was a great use of our time! There were so many great flowers, stone circles, bluebird houses, veggies, and herbs… I’ll leave you with a starkly contrasted cone flower, and a bee collecting pollen from an onion flower! Onion honey, Yum!

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I welcome your thoughts and suggestions for future posts!


4 thoughts on “If you’re struggling at work…

  1. Hi Janie,

    I hope that you are well and enjoying life AND this wonderful Summer!

    Soooo, my work life has been so cluttered that I have not had time to even read your blog…

    Something caught my eye this morning about your post (maybe it is just Monday and the title “If you’re struggling at work…”) and so I clicked through to read more. Anticipating the blog was going to solve all of my organizational problems, I was sorely disappointed to find that I had to open the “emotional work box” that I keep stored away for another time like, maybe retirement.

    “To get to a longer-term solution, it helps to get to the emotional side of what you do: How do you feel about the work you’re doing?”

    Are you offering career counseling services? lol…coundn’t resist the chance to say hello!



    • Hi John! It’s great to hear from you. I do help people get things straightened out… But you have to do the hard thinking work to figure out what truly engages you. Sometimes it’s the work you do. Often its what you do outside of work that makes you work more efficiently so you can get to the good stuff later! I hope you don’t wait until retirement to ponder the joy questions. 🙂


  2. One thought: It may not just be the physical space, but also the mental space that’s cluttered. When we take on too much work, physical space becomes a manifestation of mental space. It’s hard to know which project you should be homing in on and you find yourself “doing something” to keep at least one of the plates spinning.

    On another note, if the office is cluttered, you might suggest going someplace that isn’t, so your client can get a chunk of work done, then return to organize the office once that big piece is removed from the “to do” list. I’ve used this approach to fend off the feeling of being overwhelmed by clutter and too many half-finished projects trying to lure me off track. The important thing is to not immediately fill the void created with another giant project, but rather, to use the new found time to get a handle on the office clutter.


    • Thanks for sharing this, Jeff! I agree that a change of place can be motivating. I also notice that I do organizational work well in my home office – but find more open spaces better for creative writing. But in either space, I work better when the environment is clear. Declutter space helps me clear my mind, as you said. I like how that works. 🙂 Chat soon!


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