Let’s Work
Together 1:1!

🎟️ There are only 10 spots available in each cohort, and one of them has your name on it!

There are 10 spots available for this 3-month program. We close doors when those spots fill — whichever comes first. Our next coaching cohort kicks off the summer of 2024. Once you enroll, you lock in your rate and will be grandfathered in for life! For now, add your name to the waitlist to be the first notified when enrollment for the next cohort begins.

Assign, the third stage of the Free Time Framework, embraces three main ideas:

1. Stretch yourself to delegate ever more: There is no way you are good at everything or want to be. Rather than burying yourself in distracting details and tiny, tedious tasks, challenge yourself to assign most of what you can.

2. For every task, project, and responsibility, get clear on who will do what by when; how you will track, communicate, and renegotiate deadlines along the way.

3. Ensure that you have a central task tracking repository. Just as no information should live in any one person’s mind, no task goes untracked. Similarly, no task data lives only in messaging tools, making it harder to track and search archives in the future.

Promote Yourself From Chief Everything Officer

If you are the only person working in your business, you are far more likely to be the bottleneck and to be burdened by work that drains you. Your business may be negatively impacted by you trying to juggle all the details at the same time as forming the vision and addressing bigger challenges. Most of all, you may make mistakes or miss things by doing all the work, particularly work that you are not skilled at (and have no interest in becoming skilled at). Hiring help does not have to be overwhelming or break the bank. Start with the biggest opportunity areas related to freeing up your time and generating revenue. Build trust slowly, and increase time and team as you get more comfortable and see meaningful results.

There is a chicken-and-egg problem in the early days of any business, at least those that are not venture backed. You need to earn more money in order to hire help, but hiring help is one of the only ways you can free your valuable time to do the highest revenue-generating activities.

Construct Your Delightfully Tiny Team™

Reflect on your career and the different team sizes you have managed. When were you happiest?

Most business literature and research examines ideal team size in terms of output, what produces the highest volume and what is most efficient. I prefer to examine team size based on leader preference, culture, and cohesion. What size is most joyful for you and your team?

What makes a team delightfully tiny is up to you, the leader, to decide based on the intersection of three things: your strengths and energy, your current strategic projects, and desired outcomes for your team or business.

For creative entrepreneurs, ones for whom high net freedom is equally important to revenue growth, there is a Goldilocks quality to designing a Delightfully Tiny Team, a horseshoe of team happiness. If your team is too big or too small for your personality and preferences, you may feel dread, despair, depressed, drained, or distracted. Let’s look at both ends of the horseshoe in more detail:

Too small, and you are taxingly tiny: In many cases fewer than three people, but certainly if you are entirely solo, the burden constantly falls on you. It is hard to get the rest and recharging you need to do strategic work. You risk exhaustion and burnout from overwork and from processing the minutiae you dread, not to mention the cognitive cost of being the one in charge.

On the other end of the horseshoe, if your team is too big, you may feel burdened by pressure and complexity. Unless building a large organization is your ambition and you love managing people, recurring meetings start to overwhelm your calendar. Time spent responding to questions, switching between team members’ projects to help where they are stuck, adds up. Meanwhile, you are still on the hook for higher overhead; profit margins may be thinner despite—or because of—the growing team.

A Delightfully Tiny Team™ helps you reach a personal sweet spot of efficiency and freedom as the owner, enabling you to focus on your best work. The perfect team size for you feels, on the whole (even if not every day), delightful. You delegate the details, and have automated and systematized enough of them that even your team is not overwhelmed by minutiae. Processes are clearly defined, and team members are clear on their role and responsibilities, freeing them to take on more creative projects in the business.

In the Connection Nodes diagram below, note the difference in complexity and potential for confusion between a three-person team and a ten- or fourteen-person team. Complexity is indicated by the number of intersecting lines connecting each node to the others.

A Delightfully Tiny Team™ is big enough to share strategic work according to each person’s strengths, but not so large that they create drag and friction, for the manager or the team. High-functioning Delightfully Tiny Teams are resourceful. They know how to leverage technology, automation, and systems for their benefit. From a systems perspective every person matters, bringing unique perspectives and strengths that can improve processes with fresh eyes. If documentation is a regular practice, then brain drain becomes less of an issue. Most of all, Delightfully Tiny Teams enjoy their work! They work with joy and ease. Otherwise they would just be tiny teams: strapped, stressed, and stretched too thin.

90-Day Coaching Pop-up: How It Works

• Voxer is an asynchronous voice messaging app (think Walkie Talkies if you're not already familiar) that provides close connection while reducing scheduling overwhelm.
  

• You'll submit one question between Monday and Wednesday each week: whatever challenge is top of mind, and that would make the biggest impact in your business.
  

• I'll answer by end of day Friday that week, incorporating all the context I have from our previous work together, and any intuitive hits about what's needed most.  
  

• You are welcome to reply to my response, but I won't reply a second time — we can always save that for the following week if it's an ongoing topic/exploration.
  

• Questions don't roll over, so I suggest setting a weekly recurring reminder on your phone x 12 :)

• You will also be invited to an optional Voxer triad friendtor group: with 2-3 other business owners to share wins and ask for feedback and input in parallel to our work together.
  

• If you're not already a member of our larger Free Time community, you will also get access for three months, including a monthly live Q&A with Jenny, and a live Brilliance Barter session for hot seats with peers. You will have a chance to continue after our Voxer coaching ends at a reduced rate. 
  

• If/when I open up future cohorts, as a special offer for founding participants (anyone who starts this round) you'll be grandfathered in at your current rate even as I raise it over time.
  

• You will be billed in three monthly payments, and can cancel at any time if your business needs shift. (We don't offer refunds, but you can opt-out of month two or three, for example)