How I Get My Work Done

Today I’m going to pull back the curtain on how I structure my time as a solopreneur.

How I Get My Work Done

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(Friends, I wrote this newsletter before the most recent school shooting in Nashville, so it doesn't reflect the somber mood about gun violence many of us are feeling right now. If you'd like read what I wrote about questioning if the American Experiment was a failure after the Uvalde shooting, you can do so here.)

This week I’m departing from my regular social commentary and interviews and kicking off a two-part series, which I’m calling “Making it Happen.” Today I’m going to pull back the curtain on how I structure my time, and next week I’m going to pull back the curtain on how I make my money. Part one of this series was inspired by my friend (and Double Shift member) Jourdan who’s in the midst of a career pivot (you should definitely follow her beautiful design-focused Instagram account) where she’s creating her own schedule and work rhythm. She asked me about how I structure my time as a solopreneur. Her question made me realize that I have some hard-fought wisdom to share that could be interesting to this community, especially freelancers, solopreneurs, small business owners and those in career transition.... or anyone looking for a little work inspo. I also think transparency on work and money topics is inherently feminist and builds solidarity. You aren’t alone in your work struggles, let me assure you.

First, a few caveats. I’m not a “productivity” expert, nor do I see this newsletter as tips to be more “efficient.” I reject our society’s obsession with productivity. Instead, I want to be honest and holistic about how I get things done as a small business. I consider my work full-time, but I don’t usually work on income generating/business-related tasks a full 40 hours a week because that isn’t compatible with also doing caregiving, domestic work, community involvement, friendship and exercise.

Second, it has taken me so many years to get to a place where I felt like I have any idea what I’m doing or that I have any practical advice worth sharing about running a business. It’s been seven years since I was fired from my last full-time employer, and this is the first year I have a sustainable plan for my work life. It’s taken SEVEN years!  Most of the podcast years were chaos from a business perspective. The successes I had were the result of sheer force of will rather than thoughtful planning. My days were filled with urgent tasks with rarely any time to think of the big-picture. The way I'm working now (which has also taken many months of researching, refining and planning since the podcast ended) feels great. So today I'll breakdown how I make things happen on small scale daily level, and the bigger picture quarterly/yearly level.  

Making it Happen (daily)

  1. I’m militant about keeping my calendar updated and protecting my time. I started using the Calendly tool a few years ago which I think saves me hours every week with back-and-forth scheduling. But because it gives people lots of options for when I'm available, I'm continually tightening up when people can book time with me. Thursdays are no meetings days. I recently changed my settings so you can’t book with me before 10am in case I want to workout and so I never have to feel rushed in the morning to get to a meeting. I never make time after 5pm available for booking. I regularly block hours to have uninterrupted writing/thinking/researching time.
  2. I have a calm rhythm to my week. Mondays are my time to get myself organized for the week and write the newsletter that will go out 10 days in the future. I keep my entire Monday morning blocked on my calendar to do this. Working 7-10 days in advance gives me plenty of wiggle room in case my schedule implodes with a sick kid or any other kind of unforeseen circumstance, (which happens so often it’s basically built into my schedule.) Thursdays and Fridays I focus a lot on reading and research for my New America fellowship which is a 6 month project I need to make incremental progress on. I also like to record the audio newsletter Friday mornings. If it's late in the afternoon and I'm feeling tired or brain dead, I do dopamine-boosting quicker tasks like scheduling appointments or mundane items like camp forms.
  3. I have an Executive Assistant and I know how to use her time. Deciding I needed an assistant was a major revelation that took me six and half years to reach. I’ve successfully drilled down important things someone other than me can do, so I can focus on things only I can do. Basically, I’m delegating effectively. Let me give you some examples. I am the only person who can write this newsletter, but Haley proofreads it, adds links, and loads it into our newsletter software. I am the only person who can effectively sell myself for speaking or consulting, but Haley takes notes at my sales and planning meetings, does invoicing and financial paperwork, tracks payments and politely follows up when payments don’t come on time. She also does so much random, annoying admin like filing my LLC renewal with the Secretary of State that previously drained me and just took outsize brain space. She works five to 7 hours for me a week but honestly I feel like it gives me far more than that in time back.
  4. I keep everything organized in a Trello board. Trello is a project management software that’s free for small teams and I love it.  I check it many times a day. The system that has worked best for me is to have a daily task list, a weekly list of larger goals (no more than 3) , a list of to-dos for Haley, a list of work projects and list of personal projects. This is what it looks like:

5.  I go for walks many times a day. It clears my head, helps me think of ideas and breaks up tasks.

How I Make It Happen (quarterly/yearly)

  1. For the first time ever, I’ve made quarterly and yearly goals. Using my beloved Trello, I’ve focused on 2-3 goals per quarter, all working towards quantifiable, top line results by the end of the year. Previously when I’ve made goals, they were haphazard, overly ambitious and basically I forgot about them once I realized they might be unrealistic. When I look at this Trello board, it makes me feel calm and happy. This is a new feeling for me when thinking about professional goals. Here’s what it looks like:

Here at the end of Q1, I’m ahead on some goals and I’m rethinking a few others. I’ve already completed or have booked five paid speeches so far this year, which was my goal for all of 2023, so I’m knocking that out of the park. I’m also tracking ahead on my consulting work, and getting more inquiries. Interestingly, the consulting I thought I’d be doing (helping companies come up with comprehensive plans to support caregivers in their workplaces) is not the consulting I’m getting hired to do, which is to support mostly startup companies who work in the care space on refining their pitches, research, marketing, and branding as they sell their services to clients and investors. Honestly, the latter is better suited to my skills and I like working with entrepreneurs in the care space rather than selling my services to corporate clients. (PS if you are in the Care or FamTech space and are interested in me consulting for you, LMK!)

Q1 had a lot of goals listed that were leading towards launching a course. I’ve done some useful research on courses and got a ton of helpful input through my Double Shift reader survey. However, I’m realizing I won’t have the bandwidth to do much more with courses until at least Q3 while my New America fellowship is going, so I’m thinking or readjusting that goal trajectory. I also want to focus a bit more energy into areas that are picking up steam around speaking and consulting.

I’m tracking behind on my topline membership and newsletter signup goals but have done some good research on how to increase those numbers through the year. If you want to become a member, help me reach my goals and sign up today! And get excited for a May member drive!

2. I Have an Accountability Partner. For the first time this year, I’ve committed to having an accountability partner to check in on goals and talk through issues quarterly. I’ve never had a “peer” to do this with, and I’m loving it.  Most of my business journey I’ve felt on my own and winging it, so this has been a great way to build my braintrust around being a solopreneur.

3. I don’t shy away from networking meetings. For a long time, I always felt I didn’t have time for casual “get-to-know-yous” unless I felt like there was a clear business reason for the meeting. I’ve readjusted my stance on this, and I take three to 4 meetings with people who seem interesting per month. They are usually virtual, and I keep them at half an hour. Sometimes if I'm getting more requests than fits my schedule I’ll pass or schedule them far in advance. I have no problem declining requests from strangers who seem to want a one-way transaction of my expertise without paying for it or are just trying to sell something. Some of these meetings have resulted in paid opportunities for me, but most have not, which is ok! Doing these meetings helps me build relationships for the long haul.

As I final note, I want to share a ton of my processes from this list are the result of a program I took last year called Recognized Expert, which is run by consultant and business professor Dorie Clark. I felt like I had to swallow hard to justify spending money on a business course, but it was definitely worth it. Just wanted to give a shout out to Dorie and acknowledge that a lot of the good ideas that I’m highlighting in this newsletter didn’t come out of thin air.

For this week’s members-only thread, I’d love to hear one process you’ve tried that has improved your professional life. I look forward to hearing your hard-earned wisdom! Members-only Thursday threads are a way I show my appreciation for community members' financial support, and they are SO interesting and fun. Membership starts at $7/mo.

Just wanted to share this pic from our Double Shift members-only hangout this past weekend in Durham. is a deceitful mistress and after I'd already procured donuts and coffee it became clear the weather would not make a playground playdate possible. I instead at the last minute invited everyone to my house. Here's the pile of babies that ensued while the bigger kids made chaos upstairs.

Not pictured: three sets of twins running around my house! 

Thanks so much to our local Durham Double Shift crew for coming over and not judging me for my house being messy. It was really fun.

For more IRL and virtual hangouts, become a member. It starts at $7/mo.


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