Long To-Do List? Try this...

Long To-Do List? Try this...

42. I sighed and resigned myself to another weekend of work. 5pm on Friday was ticking closer and my to do list was still looming large. In an attempt to calm my growing anxiety, I split the list: things I needed to do for work (write proposal, send contract, craft article) and things I needed to do for life (groceries, graduation gift, call mom). While it looked visually appealing (optically less to do's!) the result was the same: 42 things needed to get done and I was in no mood to do them.

This scenario is common. So common that Kate Rosenow, CEO of Work Well With Kate, birthed an entire business out of it. Kate realized her "hot mess express" working style of long to do lists, endless hustling and weekend work had to go. She created a business dedicated to helping others streamline work and implement organizational systems. Her goal: make you less busy.

Your to do list sets the tone. If your to do's are out of control so are you. (Tweet this!) The fastest way to get them under control? Kate's aptly named "Dump Your Bag" system. For anyone (like me!) who ends up with piles of stuff in your purse or backpack (I'm looking at you half eaten granola bar, random receipts and ten pens) you can relate. Fed up with the mess, you exasperatedly turn the bag over and dump all the contents out.

The “Dump Your Bag” System:

Step 1: Dump - List every to do and task on one piece of paper. Big, small, work related, personal – write it out.

Step 2: Organize - Decide what's important versus what's urgent. You can organize the two by asking, "What happens if it doesn’t get done?" If the outcome won’t be detrimental to your work or life – skip it! Example: Mowing the lawn. It might be urgent (the grass is long!) but not important (if it doesn't get mowed it's not causing harm). Gathering your tax paperwork might not be urgent (it's not due tomorrow) but it's very important (not turning it on time could lead to fines or penalties).

Step 3: Outsource - Ask yourself, "Can a robot do this?" If so, employ software to do the work for you. Example: If you like to keep and organize receipts, HubDoc is a software that does that automatically.

Step 4. Batching - What can be grouped together and completed all at once? For example: Instead of reviewing finances every week set up a 2-hour block to do it monthly. Instead of running errands throughout the week pick one day and dedicate a longer time block to continuous errands. Kate recommends a "CEO Day" where you spend one day a month completing tasks that only you can do.

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Batching is a great way to conquer small, time-consuming to do's however I've found that bribing also works. I usually bribe myself with treats, mainly in the form of chocolate chip cookies, to keep focused and get things done.

If bribing and batching aren't working, Kate recommends the Pomodoro method which entails working for 25 minutes and resting for 5. Counting on pure will power doesn’t work. You have to plan your way out of distractions. (Tweet this!) Knowing you have a break in the future helps you stay focused in the present.


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What has been sitting on my to do list? Kate lives by her 90 Day Rule. “If something is sitting on my to-do list for 90 days or more it must be outsourced," she says. Whether it's a friend, family member, coworker or employee asking for help after 90 days is a must.

If coworkers and teammates are unavailable, freelance sites such as Fiverr, Upwork or Outsourcing With Love can be helpful when it comes to work tasks. If personal to do's can't be handed off to family members or friends, TaskRabbit and Favor are great options to look into.


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  • What have you started using lately that you’re obsessed with? Kate: HubDoc. HubDoc organizes receipts by amount and date, integrates with your credit cards and allows you to give access to an accountant - it’s amazing.
  • If you could go back in time what would you avoid when starting your business? Kate: I’d stop thinking I had to do it all myself. There are seasons of hustle and seasons of rest. You can’t have rest if you’re always hustling!
  • If you could go back in time to the beginning of 2020 what would you do differently? Kate: I would say no to more clients. I believe less stuff, better stuff.
  • What is the best gift you’ve given yourself in the last year? Kate: An online business manager.


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Try the "Dump Your Bag" exercise. If you liked that exercise, Kate has a free workshop where you can work alongside her to move from scattered to streamlined. If you sign up, let me know what you think.

To keep learning from Kate follow her on LinkedIn or Instagram.

If you enjoyed this, please share with others via Twitter, Facebook, WhatsApp or LinkedIn.

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Abdul Mazed

Freelance Writer @ Self-employed | Writing and Reviewing

3 年

Great piece! I love

回复
Leonardo De la Hoz Borrego

Founder & CEO @ LedeLab Group Oü | Co-Founder @ Grupo Protemad | Estonian e-resident | Social Entrepreneur | Sustainability Transition Management

3 年

Kim Kaupe : I recently managed to be very productive by avoiding to do lists. I prefer doing as I realize something has to be done!

Rob MacGregor

Macgregor Golf Consultants

3 年

With all due respect, nothing EVER should be on a ‘to-do’ list more than a week, absolute maximum. Ninety days on your to do list? Inconceivable and inexcusable.

Giacomo Federico Sponga

Sales Account and Administration and Business Support

3 年

Soo interesting ???

Rachael Bronstein, AFC?

Founder | Financial Coach @ Life's Jam | Accredited Financial Counselor?| Speaker

3 年

Soaking in all the hacks. Thanks, Kim! Going to check out Hubdoc right now.

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