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Each week, I tend to talk with 2-4 new “fractionally curious” people about how to break into this type of lifestyle. We typically discuss challenges and opportunities of fractional work, how to get started, how to get business, and how to brand and market the type of work that you do.
But the hardest part of fractional work isn't any of these: It’s self-moderating your time for yourself, your business, and your personal goals.
In a typical company, you have a natural heartbeat or cadence to keep you grounded. Maybe that company’s so-called “operating system” includes a weekly meeting, a daily standup, quarterly OKRs, and an annual offsite. Maybe someone else sets the agenda for each of those meetings and reminds you when you need to fill in your agenda items. Maybe someone blocks time on your calendar to participate in 1-1 feedback sessions, retrospectives, and annual reviews.
But as a fractional worker, you have none of these things. Worse yet, if you’re not careful, you get sucked into other people’s operating systems. A few months back, I hit my all-time record of 12 meetings in a single day. (Yikes.)
The best way to figure out your personal time-keeping cadence is to throw yourself into a few projects and see what breaks. Here are a few things that have helped me over the years.
Developing your own time-keeping rhythm is crucial for success in fractional work. If you’re thinking of working fractionally and you’ve never operated outside of someone else’s time-keeping system before, this lifestyle is going to be a rude awakening for you.
Time-keeping is a habit and a muscle that takes time to build. (If you need help making this a habit, then I suggest starting by reading another great book, Atomic Habits.)
In the decade or so that I’ve been taking on increasingly less structured roles in my life, I’ve tried to hone what an ideal “work output” looks like on the following time-keeping periods: Daily, Weekly, Monthly, and Seasonally.
Here are some questions you can ask yourself about each to help you get a handle on your own natural circadian work rhythms, so to speak.
The daily time-keeping period is obviously the most volatile because no two days of a fractional worker look the same. But if you can’t figure out how to start a day with a to-do list and end a day with more items checked off that to-do list, you’re really going to struggle to work in a portfolio career long-term. (By the way, if you’re just getting started, I’d suggest a calendar audit as a helpful first step. I first did this exercise about 6 years ago and tend to repeat it anytime my schedule meaningfully changes with a new project or set of projects.)
Daily Time-Keeping: Questions to Ask Yourself:
When do I like to start and end my day?
Am I more productive in the morning or at night?
How much time do I need in “email / communications triage” each day to clear my inbox?
What percent of my day is my ideal target for being on calls or in collaborative sessions vs. getting work done?
What are other important things that I like to have happen on a typical day?
The weekly time-keeping period is where I see most fractional people and early entrepreneurs fall off the rails. A week breezes by so quickly, and if you’re not careful, you might wind up every Monday with the same list of “action items” that you failed to complete from the week before. The weekly period is about protecting the time you know you need to produce high personal output, while also ensuring that you have just enough check-ins with your project teams to feel a heartbeat. You’ll know you’ve achieved a strong weekly cadence when you start to establish things like “calendar blocks” for deep work.
Weekly Time-Keeping: Questions to Ask Yourself:
How much work output do I want to be able to get out the door by Friday each week?
What do I need to hold myself accountable to getting this work done?
How much “deep work” time do I need to block in a week in order for me to meaningfully move forward on these projects?
How many times each week do I need to “check in” with my project teams in order to still move things forward?
What percent of my meeting time each week should I be dedicating toward each project team? How can I hold myself to that?
How can I signal to other people what my weekly calendar cadence looks like without being too disruptive?
How many days a week do I need solo time vs. collaborative time?
How many nights a week do I want to be out after work hours?
A monthly time-keeping period of work is the toughest one to quantify as an individual, but I’ve found it’s the most common unit of measurement among new project teams. People constantly ask me things like, “What can we get out the door a month from now?” Or: “Let’s start with a 30-day discovery plan on this project.” As a result, you might think about your monthly time-keeping as the baseline metric for how you price and staff and client work. If you don’t know what you can get done in a month (and how many hours a week it requires), then you won’t be able to effectively price yourself or estimate your time.
Another note on monthly work: Some good advice I got early into my fractional work career was to always have a “backup personal project” at the ready to sub in for any paid client work in months that are a little slower. This is how, over the past couple of years, I’ve been able to do things like rebrand myself, make a new website, get headshots, and reignite my blog.
Monthly Time-Keeping: Questions to Ask Yourself:
What are the end deliverables that this project or team needs to see by the end of the month?
How do my weekly outputs ladder up to accomplish that end-of-month goal?
How much time do I need to dedicate each week in order to set myself up for success in achieving that monthly goal?
How does the “life phase” of a project impact how much work is expected this month?
How much of my work this month is in net new “startup projects” vs. continuing projects in maintenance mode?
How will any OOO time this month impact my ability to get work done?
How might my monthly time-keeping change with each new client?
If I have less client work than usual, what are other things I can do to move my business or brand forward this month?
Ok this is my favorite time-keeping period to think about. But it’s also the most vague. The question is simply: How long does it take you, to effectively complete one so-called “cycle of work” for any one of your projects or teams? It’s tricky to define because a “cycle” means something different for everyone. And also, everyone’s time-keeping pace varies so much. But once you figure out your target “season of work” or cycle length, you’ll be able to get better at predicting when you’ll be ready to take on a new client vs. continue with an old one.
Here’s how I define it. How long does it take me to come in, net new to a project team, understand the problem or growth need they have, come up with an opinionated action-oriented plan, and then execute against the “first pilot” of that work? For me, this is about nine months. I now price my project work in 9-month increments, often with either a 30-day or 90-day discovery phase.
Seasonal Time-Keeping: Questions to Ask Yourself:
What does a completed work cycle look like for you?
What are examples of projects you’ve taken on from start to finish? How long did that take?
What are examples of other companies or project teams that might benefit from a cycle season of that length of time?
How much time do you need to invest in a new project at the “startup” or discovery phase of work vs. the maintenance or tactical execution phase of work?
How many projects or cycles can you work on simultaneously?
How often do you like to change seasons or cycles of work?
What elements or project work themes are most important for you to pursue in this cycle?
If you’re considering pursuing a Portfolio Life or any Pathless Path (both excellent books), it’s so important to have a strong grasp on your personal time-keeping cadence. I hope some of these questions (while intentionally overly structured) will help you find a way to “self audit” your own target cadence. The result may surprise you.
About a year ago, I sat down at my personal offsite update (an annual tradition I have), cleared my head, and asked, point-blank: “What would my dream, ‘day in the life’ look like in an ideal work-life balance? What are the elements it would include?”
I wrote them all down in a long list. It included work things, family things, a walk in the park. Time for deep work and time for collaborative work. When I reviewed my list, I laughed. I had just described that previous Monday.
That’s what it feels like to know you’ve got a good handle on keeping time.
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