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Multi-Hustle Time Management: From Overwhelm to Momentum with Deep Work – Pt Two

Overwhelm was hard to cop to. I wanted to say, “I’ve got it,” and be believed. Trusted. I didn’t want to admit that I was unhappy. That I felt mismanaged and that I was in turn, mismanaging. That I was lonely. Isolated in stress. Distracted. In pain.

Because that’s what it is, right? Overwhelm is painful.

It’s a voice that whispers, “You’re failing.”

“You don’t got it.”

“You are dropping the ball.”

“You’re about to be let go.”

“This isn’t working.” 

One of the longest walks I’ve taken in my life has been the one where I learn to respect my limitations, instead of pushing myself beyond my own brink in a malformed effort towards, “better performance.” This goes for my career, my health and fitness, and my relationships.

Sometimes enough is exactly that: enough. You are enough. I am enough. It is enough.

In Part One of this post series I explored strengths, weaknesses, and how to Get Shit Done when managing multiple hustles. In Part Two, I’m going for the jugular of one of the strongest voices of shame I’ve carried since third grade: the one that tells me I can’t focus. I’m too distracted. I have attention deficit.

I read a few statistics on actual Adult ADHD. 4.4% of adults have it and only 20% of those seek help for it. According to Mayo Clinic, the symptoms are as follows:

  • Impulsiveness
  • Disorganization and problems prioritizing
  • Poor time management skills
  • Problems focusing on a task
  • Trouble multitasking
  • Excessive activity or restlessness
  • Poor planning
  • Low frustration tolerance
  • Frequent mood swings
  • Problems following through and completing tasks
  • Hot temper
  • Trouble coping with stress

I suspect one reason why such a large percentage of those struggling with attention and focus issues don’t seek help might be because this list of symptoms could just as easily describe depression, the effects of chronic insomnia or poor nutrition, a harried technological society, grief or overwhelm. I guess that makes the point for diagnosis via Dr. Google. Don’t trust it. See an actual doctor. If you’re a chronic over-performer, you’ve probably tried a few home remedies too. Maybe you got here through one of them, such as a Google search for “better time management.” Maybe you, like me, suspect you don’t have ADHD because you can focus when you want to, such as when reading or doing something you love, or when you aren’t gobsmacked with over-commitment and high expectations.

To recap from Part One, its easy for multi-passionate entrepreneurs and employees managing side-hustles to fall into overwhelm. This is true even if they love everything they’re doing. Sometimes too much is just too much. My writing coach, Jamie Morris, helped me break this down into 3 steps:

  1. The Monster To Do List
  2. The Categorized To Do List
  3. The 2-Week Project Hopper

And then, you eat all the frogs. (The frog is the task you most want to avoid. Eat it first. Then go on to next.) That actually solves six of the symptoms listed above. Want to see how it worked in real time? Here’s the Project Hopper from my first two-week period:

    1. Outline modern retelling of Job WIP
    2. Outline fictionalized memoir WIP
    3. Redesign home page for Giantess Press
    4. Write copy for service pages
    5. Draft Narrative contest entry
    1. Purchase ISBN and barcode for client
    2. Send cover template to designer
    3. Write back cover copy
    4. Rewrite blog post headlines for client
    5. Comparison shop new book layout software
    1. Little Quotes meeting
    2. Pocket Writing Coach meeting
    3. Little Quotes POD research and price quotes
    4. Write Project Brief for PWC from meeting notes
    5. Update collaborative novel team
    1. Finish homeschool portfolios
    2. Set up review meetings
    3. Pack and ship eBay sales
    4. Book school physicals
    5. Business course progress

Five out of twenty tasks crossed off before my next planning period meant sister got some shit done! Some of those undone tasks were moved, some weren’t relevant in two-week’s time anymore.

This task prioritization is only part of the attention-span scenario though. Getting shit done requires staying focused and, while it helps to parse down monster to-do lists into manageable frog-bites, it doesn’t entirely solve the symptoms of ADHD or overwhelm. That requires Deep Work. 

I first read Cal Newport’s Deep Work a year ago and it had a radical impact on my concentration habits. “Deep work is the ability to focus without distraction on a cognitively demanding task. It’s a skill that allows you to quickly master complicated information and produce better results in less time.”

Going deep is a lost art. To get it back, Newport shows readers how to divide their tasks into deep and shallow, and then set timed boundaries for focus sessions. This method hit me like ketchup on a hot dog. Like hot fudge syrup on a scoop of ice cream. Like Taco Bell after the pot munchies. (Settle down, I’m a medical user for migraines! At the moment, I’m just too hungry for non-food related similes.)

By practicing Deep Work, I lightened my stress load. I got more done. I felt free to focus on the task at hand and ONLY the task at hand because I had confidence that the task belonged to this particular time window– and nothing else did. The sequential order snowballed and I did indeed feel less distracted.

Neither solution was enough to solve the problem of Overwhelm on its own. I needed them both. Once I realized I could apply Deep Work to the items on my 2-Week Project Hopper list, I stumbled onto the insight I’d craved for thirty years strong. I do not not have an attention problem. I do not have Adult ADHD. And even if I did, these two strategies in tandem create a helluva coping mechanism and an unmedicated way to break through.

Are you trying to pay attention to too many things?

I’d like to issue my fellow entrepreneurs a challenge. I’d like to hashtag it and promote it. Create a movement. A Get Shit Done Movement. Wouldn’t that be fun? There’s just one teensy snag with that though and it comes back to my current Project Hopper list.

When I look at my categorized list in order to break it down to the “Must Do’s” for the next two weeks, it includes a traditional job search. That’s because in the time that’s lapsed between Part One and Part Two of this series, I’ve made a few decisions, and one of them is that I need to have a forward eye towards my husband’s retirement and prioritize a job that offers health benefits. This is one of my favorite things about the 2-Week planning cycle. When circumstances change or clarify, it’s not derailing to make adjustments. I have full understanding about what projects I need to complete: client work. What will be ongoing: writing, my art website, freelancing. What is on the Monster List but may not make it into the Hopper for awhile: business courses and collaborations.

This means that just because I had a fun idea, I will not be buying another domain name, creating a series of graphics, or rallying my fellow distractees for a GSD month long challenge. Nope. Not gonna do it.

Even though people who write posts on topics are supposed to be authorities on the subject, I’m just gonna go ahead and make it clear that I’m not an expert on time management. I’m a curiosity-driven idea-maker that is learning as I go and I enjoy transparency in the process. I like to share what I’ve learned and I hope that in so doing, I empower someone else to feel freer, better, more capable, or relieved. Ideas are like cookies: they’re for sharing. Over the past few months, this combination of Task Prioritization and Deep Work has helped me Get Shit Done and healed my Overwhelm in the following ways:

  • I stopped trying to “do it all, all at the same time.”
  • I scheduled planning sessions every two weeks as appointments with myself to stay on track.
  • When the writing bug bit me big time on my manuscript, I knew what to adjust so that I could devote my time almost entirely to my novel. The result was a 60k word week without any feeling of failure in my other categories!
  •  I finished homeschooling. Graduated one son. Enrolled the other in school.
  • I sold a lot of stuff on eBay (and will never do that again.)
  • I rediscovered my love of painting, created several pieces, built an art website, and launched it.
  • I took five days off to enjoy my visiting family, cook, read, relax, and dance.
  • I turned down two massive projects. I said no!
  • I took two personal afternoons. I still need to work on this one quite a bit. The boundary around me-time is too porous and its easy for other demands to seep in.

I suspect the coming month to contain some fairly radical life change. One adjustment I’ve considered making is moving my planning session to a single week rather than two during high transition times. I’m not sure about that though. It reeks of over-commitment and my belly clenches, a sure fire sign that I’ll be tempted to cram too much onto a weekly list. A two-week list allows for open time windows, with hidden moments for boredom and day dreaming, like finding extra change in a forgotten pocket. I can’t overly manage a two-week list if I’ve done my monster-break-down first. I can definitely overly cram a seven day week. This might be an identification of my addiction, I don’t know. But with my lifelong tendency and family-of-origin pattern of overwork, I need to tread carefully when getting gleeful about how much more I can pack into a shortened timeline.

Can you relate?

In pencil, love, and pages,


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Going From Overwhelm to Gaining Momentum: Time Management for Multi-Hustlers is a three part blog series and a book with additional content, coming in 2019.


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