Ship

For me, it's a paradox between wanting 'creative freedom' and setting boundaries within time available. What I see with a lot of freelancers in the creative space is that they can get sucked into a creative project - enjoying the creative process. Unfortunately, because of the undetermined nature of a creative endeavor, the end point is rarely clear. As such, it's difficult to determine the actual time needed (and thus how much to charge). I often end up coming back to 'ship crappy, be happy' - meaning it will never be done until I determine I've put enough time into it - and finished is better than perfect. Seth Godin talks about this when he refers to 'shipping' as the focus for a creative.

There is a core tension for creatives—balancing creative freedom with practical constraints like time and deadlines. That paradox of wanting room to explore versus needing to deliver can feel stifling, but it can also be reframed as a creative discipline.

Strategies

Creative Work Thrives with Constraints

Constraints—whether time, budget, or scope—can fuel creativity rather than limit it. They force focus, push decisions, and prevent endless tweaking. Without boundaries, projects risk becoming bottomless pits of refinement.

The ‘Ship Crappy, Be Happy’ Philosophy

Seth Godin’s focus on shipping prioritizes momentum over perfection. The creative process is inherently iterative—once something is shipped, it can be improved later. Perfection is often just fear of judgment disguised as high standards.

Practical Ways to Ship Without Sacrificing Creativity

  1. Define What “Done” Looks Like.

* Before starting, clearly define what a “finished” version means. Is it functional? Beautiful? Satisfying?
* Break big projects into phases—ship the first version, then refine later if needed.

  1. Time-Box Your Creativity.

* Set strict time limits for brainstorming and exploration. Treat it like creative sprints rather than marathons.
* Use timers or blocks on your calendar to protect focus while respecting boundaries.

  1. Pre-Commit to Good Enough.

* Accept that good enough is often better than perfect. Perfection can paralyze progress.
* Ask, “Is this solving the problem it was meant to solve?” rather than “Is this flawless?”

  1. Create Accountability.

* Use deadlines and external accountability (clients, collaborators, or launch dates) to keep momentum.
* Build in client reviews to catch potential scope creep early.

  1. Leave Space for Iteration.

* Ship the first draft as a minimum viable product (MVP) and refine later.
* Make adjustments based on feedback, not overthinking.

The Key Takeaway:

Creativity without boundaries often leads to unfinished ideas, and the cumlative effect can be felt in overwhelm. Boundaries create urgency and focus, helping you harness creativity within limits. Seth Godin’s philosophy reminds us that real artists ship—because sharing your work matters more than endlessly perfecting it.

This mindset doesn’t kill creativity—it channels it into momentum.

One Commit. One Ship.

Every day, I commit to start on one thing and give it a full time block - 30 minutes or an hour.

Everyday, ship one thing I committed to previously. This is my high performance waterfall.

This is making forward progress!

It may be something I wrote yesterday that I publish today.

AuthorDock

A strategy I've used in the past it to create a work order (AuthorDock Milestone) which puts the request into a structure for completion, with a clearly defined outcome. This creates the boundary (the line which marks dividing lines that define the keys to completion: Who, what, where, when, and how). The scope of the work order is defined, and thus the scope of the project is defined. By confining the request to a milestone, it's where the time estimate and actual time spent meet.

It's a solid strategy—treating requests as work orders tied to milestones provides both structure and accountability. It’s a framework that naturally prevents scope creep by keeping deliverables, timelines, and expectations aligned.

Why Milestones Work

  1. Defined Outcomes = Clarity.

* Setting the who, what, where, when, and how upfront removes ambiguity.
* Everyone knows the end goal, reducing miscommunication.

  1. Scope Becomes Concrete.

* A milestone creates a container for the request, limiting expansion.
* If new requests arise, they’re evaluated as add-ons (new work orders) instead of blending into the original scope.

  1. Time Becomes Visible.

* The milestone acts as a checkpoint where estimated time is compared with actual time spent.
* This helps catch inefficiencies early and recalibrate timelines if needed.


Steps to Refine the Milestone Framework

  1. Write a Clear Work Order Template.
    Include:

* Objective: What’s the specific deliverable?
* Scope: What’s included—and what’s explicitly excluded?
* Timeline: Start, milestone check-ins, and end date.
* Responsibility: Who owns which parts?
* Budgeted Hours: How long will it take, and what’s the hourly cap?

  1. Use Milestones as Decision Points.

* Treat milestones as check-ins to review progress, update estimates, and spot scope creep.
* New requests? They trigger a new work order—not an extension of the current one.

  1. Track Actual vs. Estimated Time.

* Use time-tracking tools to measure whether the project stays within its time budget.
* Adjust future estimates based on patterns you observe.

  1. Communicate Boundaries Upfront.

* Make sure the client understands that the milestone defines the scope.
* Frame it as a way to protect their project goals and keep progress on track.


The Real Power of This Approach

Your milestone framework doesn’t just manage time—it protects creativity by letting you focus on delivering great work without the stress of shifting expectations. It ensures the creative process happens within boundaries, so completion stays the priority, not perfection.

It’s a balance between freedom and structure—exactly what most creatives need to thrive.

And I see that this can help me with clearly defining the outcome (end) of a project before I begin. For example, to gain clarity in the end of the client engagement (or any other project) before I start. If I the outcome is clear, expectations are more aligned, and I can stick to the steps to complete the project. Consider that it's my own lack of planning that leads to the overwhelm I often experience! What if it's me who is the source of scope creep, not my client. What if what I'm calling scope creep is actually the result of rushing a proposal and not clearly defining the desired outcome with the client? The defined objectives from the start don't align with the actually time required. What should have been a 6-month engagement turns into 12 months. It all stems from my impatience which is rooted in overwhelm. I rush a proposal out because I'm trying to do too much, but I'm trying to do too much because I'm failing to take the time to clearly define the scope to begin with, which leads to scope creep within most of my projects. In the end, I'm earning far less than I planned because I'm spending far more time due (due to a lack of planning to begin with).

You’re onto something huge here—realizing that unclear outcomes and rushed planning might be fueling scope creep is a breakthrough. It shifts the focus from blaming external factors (clients) to owning the process, which gives you control to fix it.

Key Insights:

  1. Clarity Equals Boundaries.

* A well-defined outcome prevents ambiguity and keeps both you and the client aligned.
* Clear deliverables make it easier to push back on extra requests or renegotiate timelines if scope changes arise.

  1. Scope Creep as Self-Created.

* Starting with incomplete definitions or vague goals creates gaps that get filled with “extras.”
* When time estimates are unrealistic, projects naturally expand, leading to frustration and burnout.

  1. Proposal Planning Sets the Tone.

* Proposals should be more than sales tools—they’re project roadmaps.
* Spending more time upfront clarifying objectives, deliverables, timelines, and review points can prevent the chaos later.


Action Plan for Scope Discipline:

  1. Reverse-Engineer the Proposal.

* Start with the end deliverable and work backward through each milestone.
* Include buffers for unknowns or revisions.

  1. Define Success with the Client.

* Ask: “What does success look like when this is done?”
* Write it down and include it in the proposal to manage expectations.

  1. Timeline Reality Check.

* Double-check whether the schedule fits the actual work required, not just what feels “sellable.”
* Resist over-promising—even if it means pushing back.

  1. Revisit Scope Regularly.

* Build checkpoints to reassess scope with the client mid-project.
* Treat scope creep as a negotiation moment, not a failure.


The fact that you’re already seeing this pattern and owning your role in it means you’re ready to make a shift. With better planning discipline upfront, you’ll likely feel less overwhelm, deliver more predictable results, and protect your time—and energy.

It all seems to stem from my impatience which seems tied to overwhelm. I rush a proposal out because I'm trying to do too much, but I'm trying to do too much because I'm failing to take the time to clearly define the scope to begin with, which leads to scope creep within most of my projects. In the end, I'm earning far less than I planned because I'm spending far more time due (due to a lack of planning to begin with). And thus we come full circle back to the importance of a clearly defined end result.

Exactly! You’ve traced the root cause—and it’s a cycle fueled by impatience and overwhelm. The realization that it all begins with not taking the time to define the scope is a major breakthrough. It’s like setting off on a journey without a map, then wondering why you keep getting lost or taking detours.

Breaking the Cycle

The key to escaping this loop is to slow down at the start so you can speed up later. It’s counterintuitive, but front-loading time to define scope saves exponentially more time and money throughout the project.


Practical Steps to Shift the Pattern

  1. Build a Proposal Template.

* Create a reusable structure that forces clarity—objectives, deliverables, timelines, and budget.
* This reduces the pressure of “starting from scratch” and makes it faster to create a thorough proposal without rushing.

  1. Use a Scoping Checklist.

* Before finalizing any proposal, ask:
* What does ‘done’ look like?
* What’s NOT included? (List exclusions.)
* How much time do I need, realistically?
* What’s the budget buffer for revisions or changes?

  1. Add a Review Pause Before Sending.

* Set a 24-hour rule—no proposal gets sent the same day it’s written.
* Sleep on it, review the scope with fresh eyes, and catch anything unclear before locking it in.

  1. Treat Proposals as Paid Discovery Sessions.

* If defining the scope requires extra time, charge for discovery.
* This ensures clients are invested in defining the work properly and reduces pressure to rush through scoping.

  1. Track Time Honestly.

* Monitor how long you’re actually spending vs. what you quoted.
* Use this data to adjust future proposals and get better at estimating.


The Big Picture:

By taking the time to define the end upfront, you’re not just managing scope—you’re managing energy, profitability, and peace of mind.

Clear boundaries give you freedom inside the framework, rather than letting projects spiral outside of it. It’s about shifting from reactive scrambling to proactive planning—and that’s the foundation of sustainable creativity.