Coffee Talk

Almost a year after I made the leap to entrepreneurship, I met a former colleague for coffee.

He asked, “What’s the biggest difference between your day-to-day now and your corporate job?”

I replied with a question of my own:

“How much time do you spend on tasks directly related to your company’s critical path?”

“Maybe 20%”, he said.

“For me, it’s at least 80%,” I told him. “And it’s not really a choice. Most days I’m choosing between critical tasks. The extraneous ones rarely make it to the table.”

The critical path is the longest stretch of dependent activities required to achieve a project or goal.

While critical path analysis comes from project management, we’ll adapt it here for entrepreneurial goals. Starting a business or launching a new initiative carries far more uncertainty than a typical corporate IT rollout or real estate project.

The aim of defining and executing a critical path is simple. Perform the activities that turn the unknowns into knowns as quickly as possible.

For some, this process or its results may seem obvious or unneccesary.

However, there is a familiar story about the would-be entrepreneur who spends their first weeks or months designing logos or filing incorporation documents.

We’ve all done this. We spend precious time and resources on things that don’t matter.

“But don’t those things need to get done at some point?” Maybe, but they’re rarely critical to your success.

The weeks or months lost on non-critical endeavors destroy momentum while quietly killing your business.

How do you define, stick to and ultimately execute the critical path to make your business succeed?

I recently advised a creator launching a humor-and-entertainment-focused YouTube channel. Their target: $5,000 MRR ($60k ARR) within a year.

Not impossible, but aggressive. Here’s the analysis we used to define their critical path.

The Critical Path

Step 1: Identify a Likely Path

The first step is to map a likely path for how your project will evolve. Start with the end in mind and work backward.

In this case, the target is $5,000 in monthly recurring revenue.

For a humor-focused YouTube channel, a reasonable 12-month scenario might look like this (assuming 10,000 subscribers):

To get to these numbers in 12 months, we approximate the conversion rates for similar YouTube channels which equates to:

• Fan Support: 1% conversion rate @ $5 per month

• Merchandise: 1% conversion rate @ $25 profit per item

• Sponsorships: 2 @$500 per month

• Ad Revenue: 200,000 monthly views at $5 cpm

The mix will almost certainly be different in the end. Especially with edgier content that may earn less from ads, but the point isn’t precision. It’s to sketch a realistic scenario so you can define the critical path.

Most people stop after this step. Don’t.

Step 2: Identify the Core Unknown

Start by listing your knowns and unknowns.

From our creator:

Knowns:

• Basic idea for character, story, and hooks

• Plaftorm - YouTube

• Current production capacity - 1 video per week

Unknowns:

• Will the content resonate with an audience?

• How will the channel monetize?

Then, look for dependencies. In this case, the first unknown, Will anyone like the videos? is the priority. It’s the “product–market fit” question, and it usually comes first in most entrepreneurial projects.

Monetization can wait. You need viewers before you can earn from them.

Core unknown: Will people like the videos?

Step 3: Unravel the Core

In Step 2, we identified the core unknown: Will the content find a receptive audience?

As with sales calls or free throws, success comes from reps. The fastest way to learn if an idea works is to produce as much as possible, as quickly as possible.

Listing knowns also reveals constraints. Here, the creator can currently produce 1 video per week—that’s 52 videos in a year.

What if they increase their output?

• 1 per week = 52 videos

• 3 per week = 156 videos

• 5 per week = 260 videos

Even if 5 per week isn’t realistic, increasing output dramatically improves the odds of finding an audience.

For your own project:

• What knowns are actually constraints?

• What’s your core unknown?

• What one process could you go all in on to make the unknown known and tilt the odds in your favor?

Step 4: Describing the Critical Path

For our YouTube creator, the critical path is improving their video creation process by:

• Mapping the current 1-video-per-week workflow

• Auditing each step for time and effort

• Listing all inputs—tools, techniques, resources

• Identifying the steps that would provide the most leverage if improved

• Building a plan and iterating on each step

Several bottlenecks emerged quickly. Most notably, an inefficient illustration process caused by unfamiliarity with their software, along with other smaller issues.

The priority is clear: focus solely on improving production until they can consistently produce 3–5 videos per week.

Even if you know your critical path are you giving it your full focus?

Step 5: Executing the Critical Path

“What gets measured gets managed.”

You must define metrics to gauge your progress.

For our creator they are the following:

• Videos per week

• Total minutes required to produce one video

• Total minutes per major step (illustration, animation, audio, etc.)

• Total steps (ie can steps be eliminated or outsourced?)

As the creator monitors these each week, they will see how and if progress or setbacks are occurring.

How can you define both aggregate and detailed metrics to track your progress?

Step 6: Staying on the Critical Path

Identifying your critical path is easy. Sticking to it is hard. Three common de-railers I’ve noticed in myself and others:

Fear of Failure

The critical path is the fastest route to feedback and early feedback is often negative and can include; bad reviews, harsh comments, and low engagement.

Fear tempts us to work on “important” tasks that aren’t truly critical.

Remember: failure is progress. Collect the no’s and critiques as proof you’re moving forward.

Shiny Object Syndrome

The critical path can be repetitive and dull. You’ll be tempted by more exciting tasks that seem urgent. Resist. The road to failure is lined with shiny objects.

Hammer Syndrome

We gravitate to what we know, treating every problem like a nail for our hammer. Developers keep building features when they should be marketing. Writers keep editing instead of selling. The critical path is often uncomfortable. Use that discomfort as a signal you’re moving in the right direction.

The Next Step

Defining and executing your critical path saves time, conserves resources, and gets you to your goals faster.

But its value goes beyond efficiency.

You’ve heard the saying: failure isn’t failure if you learn something.

Even if our YouTube creator’s first idea flops, imagine how much more likely the next one will succeed because they’ve become a 3–5x more productive creator.

That’s the real magic of the critical path: it forces you to become a better executor.

Ideas are cheap. Execution is priceless.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.