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How do you deliberately improve the conditions under which you do your work? That is if you work on a project and things go well, how do you ensure that things continue to go well during your next project? Conversely, if you work on a project and things go poorly, how do you prevent things from going poorly during your next project?

Is this something that you even think about?

Honestly, this is not something that I have put much thought into until recently. For example, I have worked as a professional web developer for 10 years, and I cannot count the number of projects with unrealistic deadlines that have required me to work late nights and weekends. Why did I accept projects with unrealistic deadlines as an unavoidable reality for so long?

What has occurred repeatedly throughout your work that you want to change but have not changed yet?

I recently spent a lot of time thinking about the idea of deliberate improvement in the pursuit of avoiding unrealistic deadlines for future projects. I discovered that I lacked a framework that allowed me to think about and address the problems I encountered systematically.

Today I'm going to talk about the framework I used to solve my problem with unrealistic project deadlines and how this framework can be used to help you reliably improve how you work on projects as well.

Reflecting on unrealistic deadlines

I recently shared a project that I completed for Rippling, where I mentioned that the project's timeline was tight, and as a result, I was rushed to get the work finished so that the website could launch on time. What was the result? Well, we launched the website, but at a significant cost to the quality of what I was able to build, as well as my well-being while building it.

Rippling re-branding collection
Play did a wonderful job handling the re-branding for Rippling

Source: Play case study

After launching the new Rippling website, I decided to take a one-month sabbatical to unwind and reflect on the myriad of projects that I had been working on since I started freelancing. Something I kept coming back to while reflecting was the timeline for the Rippling project.

  • Why was the timeline so tight?
  • What could I have done to improve the timeline?
  • Why am I repeatedly working on projects with such unrealistic deadlines?
  • How can I prevent this from happening in the future?

I ended up answering all of these questions and then some. However, the most valuable insight I gained by thinking about that last bullet point, and it is unrelated to the idea of project timelines. In wondering how I could prevent tight deadlines from happening in the future, I ended up reflecting on why I hadn't taken the time to think critically about this issue until recently.

If project deadlines have plagued me for over a decade, why hadn't I taken the time to think about and solve this problem?

Making reflection deliberate

In a recent post, I discussed the idea of analyzing what mindset I have after completing a project. In it, I mentioned that I generally embody the "future mindset," where I find myself more inclined to look towards the next thing after completing a project, as opposed to looking back and reflecting over what I just completed.

Until recently, I spent most of my time reflecting on projects while working on them. To better demonstrate this, here is a rough outline of how reflection manifested in my process:

  1. Start working on a project
  2. Start experiencing things that are going well and going poorly with the project
  3. Have impromptu reflection on why things are going well and going poorly
  4. Loop over bullets 2--3 until the project is complete
  5. With the project completed, I look towards the next project that I want to start

What was missing from my process was taking the impromptu reflections that I had during the project's execution and making time to follow-up on them after I had completed the project. I call this time to explicitly follow-up on my thoughts deliberate reflection. The distinguishing factor is that deliberate reflection is done with intention, whereas impromptu reflection is done in-the-moment and occurs organically.

If I am always looking forward and am never looking back, how will I learn from the past to improve how I approach the future?

Building in time for deliberate reflection allows me to focus on thinking about the work, as opposed to doing the work. Creating this separation allows me more time to flesh out my thoughts, which provides me with greater clarity around my experiences and how these experiences have made me feel. Having this deep understanding is crucial when manifesting positive change in my life.

Now that I understand the value of deliberate reflection, how can I make this time productive?

My framework for deliberate reflection

Reflection is always a useful way to gain clarity around your thoughts and feelings. However, I learned that adding some structure can reliably produce something actionable from my reflections, which gives me something that I can utilize moving forward.

Below I've made an outline of the process that I use to get the most out of my deliberate reflection:

This outline might seem like a lot, but I believe that this is a natural process that allows you to take ideas that you have and turn them into something actionable. The more that you work through this framework, the more automatic each step will become.

Now, let's go over each of these steps in more detail.

Setting aside time to reflect

The first step is setting aside time for reflection after completing a project. The amount of time that I spend reflecting is commensurate with the size of whatever I just completed.

The larger the project you complete, the more time you will want to spend afterward reflecting on what you just completed.

I suggest doing your reflection somewhere that inspires you. I enjoy being out in nature when I'm reflecting, as that setting is where I have the greatest number of ideas. Pick a setting that puts you at ease and inspires you.

Picture of the Presidio in San Francisco
The Presidio is one of my favorite areas to hike in San Francisco


Picture of Baker Beach in San Francisco
I also love walking around the beach, so ,I: can frequently be found at Baker Beach


Have a brainstorming session

Now that you have space to reflect, you can begin using this time to have a brainstorming session where you allow yourself to have free-flowing thoughts about the project you just completed. You want to capture each thought by writing it somewhere (physical or digital, it doesn't matter).

You don't need to organize these thoughts yet; you just need to capture them somewhere. The point of this process is to get everything out of your head and write it somewhere so that it can be used later.

Here are some prompts that I use to start my brainstorming session:

  • What feelings do you have when you think about the project you just completed, and why do you think that these feelings exist?
  • What was on your mind as you worked through this project (i.e., what were your impromptu reflections throughout the project?)
  • What went well during the project?
  • What went poorly during the project?
  • If you could change one thing about this project, what would it be?
  • If there's one thing that you could avoid repeating in future projects, what would it be?
  • If there's one thing that you would like to repeat in your future projects, what would it be?

These prompts are designed to kickstart your critical thinking. You don't need to work through each prompt one-by-one, although you certainly can. If you have prompts that work well for you, I recommend keeping a list of them stored somewhere so that they are easy to reference.

It is also worth noting that although I will be working through this article by reflecting on an aspect of a project that went poorly, you can just as easily reflect on an aspect of a project that went well. It can feel nice to acknowledge what went well during a project, and it is also useful to understand why something went well and how you can continue this in your future projects.

Prioritizing items

Now that we have a list of items, we want to determine which item is the most important. What is the most important thing you would like to address and carry into your next project?

I acknowledge that this can be difficult, and I would advise you to avoid becoming mired in prioritizing the entire list you created. Just go with what feels right to you. To use a phrase that may or may not be helpful: "go with your gut." If your gut isn't helping you, try scanning each list to see if any item stands out to you or makes you react in a way that is different than the rest.

The point of this exercise is to understand which area of improvement is the highest priority. You cannot improve everything at once, so you need to determine where to start.

Clarifying items

Because we generated our ideas during a brainstorming session, the idea that we're working with might not be fleshed out. To fix this, we'll do another brainstorming session using the highest-priority item you decided on above.

I like to ask myself questions about a subject to get myself thinking and then answer them to produce clarity. To do that, I take the idea of "improve tight deadlines" and begin asking myself:

  • Why did we have tight deadlines in the first place?
  • Why did having a tight deadline cause me so much stress?
  • How might a better deadline have improved my ability to do my work or the quality of my work?
  • What about the deadlines could have changed such that I would be happier?
  • If I had complete control over the timeline for this project, what would that have looked like?

The point of this exercise is to gain clarity on the highest-priority thing that you want to improve. Focus your critical thinking on this one specific idea and flesh it out as much as possible.

You should continue taking notes as you work through this exercise. This ensures that you don't forget anything that you've thought of, and it allows you to reference your thoughts in the future, which may be useful when thinking about this subject.

Making items actionable

Now that you have an idea that you understand deeply, you can take this idea and turn it into something that can be utilized for future projects.

Take this idea and think: "what steps can I take to ensure that this gets incorporated into the next project that I work on?"

For example, after reflecting on the tight deadlines that I was experiencing, I thought of a few ways to improve this in my future projects:

  • Don't accept any projects with set deadlines
  • Don't accept any projects with clients who are unwilling to negotiate deadlines
  • Always map out a project timeline using the scope of work to understand what realistic deadlines look like
  • Imagine that the work will always take 1.2–1.5x the time that I expect
  • Have ownership over creating a timeline and setting deadlines for the work that I do

Now, I have turned the idea of "improve tight deadlines" into a list of actionable steps that I could utilize to improve my work.

Prioritizing actionable items

You likely generated many ideas about how to solve the problem you were encountering in the previous step. Because you cannot focus on all of these ideas at once, you need to determine which is the best option to improve your next project.

Look over the actionable items that you generated and determine which would best solve the problem that you were encountering. What is the one item that, in your ideal world, you could utilize in every single project moving forward?

I decided on: "Have ownership over creating a timeline and setting deadlines for the work that I do."

All of the other ideas were good, and I can still use them going forward. However, this idea resonated with me. If I want to mitigate the effect of tight deadlines for a project, I should have ownership of the project timeline so that I can set realistic deadlines for myself and project stakeholders.

Utilizing actionable items

Lastly, It's time to take this actionable item and use it for your next project. Your focus should be shifting away from what you would like to change to how you can manifest this change in your next project.

How will I manifest the idea of "Have ownership over creating a timeline and setting deadlines for the work that I do" in my next project?

I determined that in the "discovery phase" of communicating with a client, I will ask what their ideal project timeline is. Then, I will take the scope of work and map out what my ideal project timeline looks like. Comparing the two timelines allows me to see the degree of difference between them. If the degree of difference is drastic, I might alter the scope of work to provide a path towards meeting the client's deadline. I can then present two options to the client: one with the original scope of work that aligns with my timeline and one with an altered scope of work that aligns with their timeline.

This approach shows I am eager to work with the client using their timeline while also looking out for my best interests. If the client is unwilling to work with either option that I presented, then I know that the relationship is not worth pursuing. If they are willing to work with one of my options, then the work that I did just paid off [1].

Rinse and repeat

Congratulations! If you worked through this framework step-by-step, you should have taken an idea from being a nebulous thought to an actionable item that you can utilize in your future projects.

At this point, you can take any of the other ideas that you had during your initial brainstorming session and work through this framework to clarify and make them actionable.

You can also keep a list of the ideas that you generated during your brainstorming session and break them down into two categories: "clarified and actionable" and "needs clarification." I like to do this for myself because I never have enough time or energy in the day to work through every single item that I generated while brainstorming. Keeping a list of what can still be clarified and made actionable allows me to come back to my thoughts when I have the time and energy to continue working through them.


I hope that by reading this, you have gained some insight into how I systematically improve the conditions under which I work on projects and that you can apply some of what I've shared with your projects. My goal is to provide a framework for deliberate reflection that focuses on achieving actionable outcomes as a result.

Working through this framework starts by setting aside time to think about what has gone well or poorly during your last project. Having made this time yourself, you can have a brainstorming session and create a list of things that you would like to improve or continue doing in your future projects. From here, you can begin prioritizing the items in this list and, working with the highest-priority idea first, start to clarify your ideas so that you can gain a deeper understanding of it. After you gain an understanding of your idea, you can turn your attention towards making this idea actionable and creating a path towards incorporating it into your future projects.

There is a lot of value in setting aside time to reflect deliberately. I know firsthand how tempting it can be after finishing a project to rush to the next thing on my plate. After all, why spend time thinking about what I completed when there is so much left to do? Working with this framework has helped me adopt a mindset that frames this period for deliberate reflection as being in service of the next project that I work on, potentially enabling me to do my work with greater ease and happiness.

If you have a question about this framework or would like to share your strategy for improving your work, don't hesitate to reach out to me on Twitter or leave a comment down below.


  1. There are expectations, of course. Depending on the client and the project, I may be more or less willing to work with a tight deadline. Everything is context-dependent. ↩︎