Business Thoughts multi-hustle Time Management Tools & Teachers Writing Business

Multi-Hustle Time Management: 5 Steps to Get Shit Done. Going From Overwhelm to Gaining Momentum- Pt One

I’ve been a mother of many home educated children, an entrepreneur with multiple hustles simultaneously running, and an employee with an omnipresent side dream. All of these incarnations came with the frequent reality of more things to do in a day than time to do them all. I’m constantly inundated with a rising tide of new ideas sucking me into an undertow of overwhelm– and the honest truth is that many of those ideas are never completed while I gasp and try to tread ever-churning waters.

My daughter said, “Mom, every time I call you’re talking about a new idea.”

A former employer said, “Let’s be honest here, Tia. Sometimes you go off range.”

Which brought flashbacks from teachers who’d written on report cards, “Tia most needs to improve on finishing what she starts.”  My stomach still clenches with queasy green shame.

Maybe you can relate.

Idea makers aren’t strong in everything. Perpetually searching for what to major in, I recently took the Clifton Strengths Quiz.

No surprises there– but plenty of validation. Visionary, strategic, collaborative, full of ideas, and empathic. As a reinforcement of my strengths, their report worked well. The book encourages readers to craft lives built around their strengths, rather than bash their heads against innate walls of weakness. As a strategic visionary who is full of ideas, I’d already navigated that obstacle course. All of my hustles are built around my strengths. The fact that there are multiple hustles at all demonstrates my strengths. I like a lot of things going on at once! It invigorates me! And, I also love time to drill down and focus hard on something I love (more on that in Part 2).

But, “Lots going on” and “Time to focus” don’t exactly go hand in hand.  I needed a solution for the weaknesses that come along for the ride: time management and prioritization.

The time management content niche is eternal because lots of people have this very same problem! If you are struggling with more than just a full plate, but actually many full plates, continually and simultaneously spinning in the air, that’s not a sign of distracted weakness– it’s the nature of the beast. And, in today’s gig economy, multitaskers are spinning multiple full plates at an alarming rate. They are stay-at-home moms and work-from-home parents, moms with full time jobs outside of the home and a side hustle at home at night, homeschoolers with cottage industries, and freelancers with more than one shingle. Who has just one job anymore?

Story time: What I Need to Avoid

I recently dropped all the plates– and have spent the past few months have been trying to clean up the mess.

For the past four years I had a day job and a side dream. This day job started out as an exceptionally good fit for me because it ran like a freelance gig, with diverse projects and rotating seasons, and my role drew from all my strengths. It also, unlike freelancing, provided a steady paycheck. Most people work because they need income, and if you have any experience at all in the freelance world, you know the value of a steady gig. You’ll overlook many flaws in order to retain that necessary stability.

So, I did my job with joy and worked my side dream in the pre-dawn hours, getting up super early to write. At home, during the first year, we had four kids in four schools, and by the end, three had reached adulthood. That’s a ton of life change in a small amount of time. The pendulum swung and things changed with my job; the flaws outweighed the benefits and I took on additional side work. Now I had a day job, two side gigs, a household and family, and a writing dream actively being pursued. I spun all the plates and tried to remember to breathe. The flames of burnout tickled first my toes, then crept up my legs, until finally, they choked off my throat.

Mercy came in the form of an unexpected weekend-meeting request.

The largest plate, the day job, crashed rapidly and unexpectedly to the floor. I reeled from the loss and initially, sat for hours grieving in the sun, staring into a nebulous future I could not fathom into form.  That beloved job had become a north pole in my day, the thing that always had to come first. Without it, I felt untethered– which can be good, it can feel like freedom– but at first was incredibly disorienting. Teary weeks passed. I grew my side gigs, added some new ideas, my family supported me with kindness, my writing dream advanced, and I suddenly realized what the Strengthfinder had been trying to say:

You can’t be good at all the things and if you try, you’ll exhaust yourself from the effort. There is such a thing as spreading yourself too thin. Not every idea has to be pursued. As Marie Forleo says, “Simplify to Amplify.”

Ah, but freelancers will relate: without the steadiness of a regular paycheck, diversity rules. Even with a steady paycheck, it might not be enough to cover all the bases. Or, new passions might come up. Or, it’s just hard to say no to stuff. It’s a super-easy trap to fall into.

The strategic part of my brain is a rockstar at making lists. I might be even too good at list making, as any one who has received a project brief from me can attest. These several-page documents are how I break down monster-sized concepts into reverse-engineered baby steps. They’re full of keyword research, timelines, marketing ideas, competitor info, and lists. Common feedback from people who struggle to make big things happen (and so have hired me to do it for them) is, “Wow, that’s an overwhelming document. You use it– but I can’t bear to look at it.” Where I see order, they see Too Much Information. But, it gets the job done and so do I.

Here is where my strength beats up against my weakness. I’m awesome at taking one giant project and breaking it down into manageable bites. I’m not as awesome when there are a whole bunch of projects, like instruments in an orchestra, to harmonize into symphonic bliss, all at the same time, without completely overwhelming my senses and losing the melody altogether.

Multi-hustles within a single life require that symphonic level of organization. I needed a conductor. No, I needed to learn how to become a conductor.

Enter: the Writing Coach. 

Jamie Morris, my writing coach, is a conductor. She’s adept at what few can do: the developmental edit and organization of a novel. It boggles my mind how she does that – taking an impassioned, sensitive writer’s draft (because all writers are sensitive and impassioned), which is often a mess, and discovering a readerly order that makes everything better. Jamie sharpens stories. She’s great with details. And most of all, she’s kind and coach-y so the critique is always constructive.

She’d attended the births of all my brain children for over a year. She says she loves all the idea-kids and like a good fairy godmother, passes no judgement on any of them. But she knows when I’m indulging too many with my attention and she was there for me when I came crying about having too much to manage. Jamie knows me well and reaching this point was no surprise to her. I think, actually, she’d been waiting for my call.

Step One: List Everything You Are Doing

“Your problem is not that you can’t get things done. You get amazing things done. Your problem is that you are trying to get too many things done at one time.”

I nodded on our video call and looked down at my to-do list. It was an 8 x 11 page of paper turned sideways, full up and down and all the way across the page.

“Tell me everything you’re working on right now. Every single thing in every part of your life,” she said.

As I listed them, she was putting them into boxes. Categories. Whereas I’d had them separated by owner-client, she had them broken them more simply.

  1. MY WRITING: This included my WIP’s, contest entries, website, and the press I co-founded
  2. BOOK SERVICES: My primary shingle. I help other writers publish their books. This also includes the resource site I’m building with a fellow creative
  3. COLLABORATIONS: Currently, two projects I’m working on with teams of others
  4. HOUSEHOLD: Homeschool, admin, eBay listings, etc.

It hadn’t dawned on me to lump some of those things together. But having fewer than five categories immediately calmed the inflammation in my brain.

Step Two: Choose Immediate Priorities

My organizational approach to keep multiple plates spinning had been the same since the day my second baby was born: tend to the one screaming the loudest.

This meant that across all my columns, each day I did the items that if not done, could lead to imminent disaster. I’m not a procrastinator– I’m a firefighter. I was good at doing the unpleasant things first, what some people call, “Eating the Frogs,” so that I wasn’t just being busy to procrastinate on something I’d rather not do. But, I was still cherry-picking my favorites and continually trying to identify what could become a fire so I could put it out first.

Jamie’s next step offered a solution. “In each category, pick the things that must get done in the next two weeks.”

“But that’s all of them.”

“No, it’s not. Undoubtedly you have items on that list that have been sitting there for longer than two weeks. Items that carry over from list to list. Choose the big things that absolutely must get done in the next fourteen days.”

When I was done, each of my categories had about ten items. Here’s a sampling:

    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

Technically, the business courses and webinars I’m taking aren’t household or miscellaneous. But they are so general that it seemed that was the best place to put them. Each of these categories contained appointments and other items not listed here. It still seemed like an incredible amount of work to accomplish and yet, less than what I’d been trying to do before.

Step Three: Planning Takes Time, So Plan For It

Jamie’s next piece of advice wasn’t related to the list or the things on it, but it was crucial.

“You need to plan for time off.”

Whojahwhat? Time off? With this list?”

“Yes. And, I’m not talking about vacation, although you need that too. You need a weekly window of time off, ideally out of the house, to do two things: refill your creativity tank and assess your progress.”

She told me to find the date 14 days from now and another one 30 days from now. “Those are your planning days,” she said. Jamie recommended taking my planner and going to the coffee shop or book store so I wouldn’t be distracted but since my white board and calendars are in my office, I knew that’s where I’d strategize.

“The weeks in between are your personal days. You need at least a 3 hour window. Go peruse antique stores. Go to the movies. Wander the bookstore. Do things that stoke your creative fire and air out your mind.”

I choked up a little when she said that. Our home is in an area peppered with antique malls and I’m always wondering about them and telling myself I’m too busy, I don’t deserve to take time off when there’s money to be made and tasks to be done. Going to the movies alone in the middle of the day is my FAVORITE thing to do, but likewise– I almost never allow myself to indulge. Now this professional was instructing me to write it on my calendar and helping me carve a new lifestyle that depended on these windows of time in order to function.

Step Four: Say No to everything else.

“Anything not on that categorized list gets put off. You say no. You say not yet. You say later.” Jamie’s tone was absolutely firm, with the tough-love part of her coaching demeanor coming through strong. This was the, “Yes, Ma’am” moment with the marching orders.

This was a remarkable step! Fourteen days feels like nothing. It’s a sneeze. Anything that didn’t fit on my list could easily wait for fourteen calendar days. That’s usually within the same month. It’s at least within reach. Perception is everything on Step Four. I didn’t feel like I was putting things off– I was prioritizing. I was staying on task. I was focusing. I was crossing things off my list and building momentum.

Which led me to realize…

Step Five: Get Shit Done

On the first day, I chose all the frogs. I mean, technically we’d already chosen the frogs from the really big list, the items threatening to transform from frogs into infernos if I didn’t hop to it. But within the list in Step Two were the time sensitive frogs, the frogs that triggered other tasks, and the frogs I loved to hate so I kept them around for too long.

eBay, for example. I hate listing and selling things on eBay. But, when my Spring income wasn’t what I’d been expecting, I decided to sell some stuff to finance more hustle-building time. That’s a time-hog of a process and it almost never proves as lucrative as hoped. Still, I had a pile of homeschool curriculum to list, electronics, books, curtains still in their packages, and unopened board games. It felt counter-intuitive to start my Monday with eBay listings when all those “workier” tasks sat waiting. But eBay was THE FROG May most needed me to conquer, so it could take all month to process bids, receive payments, send for shipping, etc. I needed eBay working in the background, earning me money while I took care of other business. And, it worked!

Would I have actually done it without the new system? Probably not. And, because I did, I gave myself an entire six weeks more of paid bills.

After the eBay frog, I clicked on down the list. It felt exactly like working from any other task list. Do it, check it, move onto the next thing. What was different was the organization. I could feel a progressive shift within each category column. I wasn’t getting disjointed by pulling more attractive tasks from the bottom of my lists. All the randomness was gone and so was something else – the anxiety from overwhelm each time I looked at my list.

The initial take-away:

Sometimes when it feels like there’s too much to do, it’s because THERE IS TOO MUCH TO DO. Multi-hustlers can’t always remove gigs from their lists (although sometimes they can– refer to step four). What you do have power over is the perception you create for yourself with your approach to organization. 

When I began this restructuring, I didn’t realize I was weeks away from a critical breakthrough that would impact my whole being (for the good!).  I was just taking that old Al Anon advice to, “Do the Next Right Thing,” and following my coach’s instructions. The lessons I learned the first week felt big until I rounded the bend on the month and discovered giants beyond those hills, Giants with names like, “What You’ve Been Searching For,” and “Oh, That’s How They Do It.”

Stay tuned for Part Two!

In pencil, love, and pages,


Don’t want to miss the series? Subscribe!


* indicates required

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.






1 Comment

  1. Time Management for Multi-Passionate Entrepreneurs: From Overwhelm to Momentum with Deep Work

    August 6, 2019 at 9:27 pm

    […] Part One of this post series I explored strengths, weaknesses, and how to Get Shit Done when managing […]

Leave a Reply