Josh Bavari's Thoughts

Thoughts on technology and philosophy

Start Finishing - Book Review

about a 15 minute read

I’m currently diving into a book recommended by Seth Godin – Start Finishing. This book is primarily aimed at supplying people with additional approachs to tackling ‘important problems’.

Part 1 – Clearing the decks for your best work

Chapter 1 “Someday” can be today

Charlie drives right to the point – you know what your best work is, and when you are not doing it. We thrive when we do our best work. Best work is defined as work that is important to you. Your best work also requires dropping the busy work and focusing on the work. The more important to you, the easier it is to get displaced by other things.

Best work projects generally take 3 to 5 years.

No ideas, only projects

Throughout the book, the author Charlie Gilkey describes that there are no ideas that we work on, we work on projects. The important part here being, deciding what we need to do to complete these projects. By figuring out what we say no to, we can say yes to the right things. This book starts by breaking down some systems one can take to figure out what the right things are, they ‘burying’ the rest.

Chapter 2 – Getting to your best work

Charlie talks about the ‘air sandwich’ – which is a gap between your vision, mission, purpose, and big goals being one side of the slice of bread. The other being your day-to-day reality. Between these slices lies the air sandwich.

These are created from:

  • Competing priorities
  • Head trash
  • No realistic plan
  • Too few resources
  • Poor team alignment

Head trash is pretty straight forward, it’s the negative thoughts you tell yourself. Cut that crap out!

You can combat the 5 issues above with:

  • Intention
  • Awareness
  • Boundaries
  • Courage
  • Discipline

A good tip here that Charlie suggests is tryign to align competing priorities. He also suggests taking out the head trash by being aware of it, having the backbone to challenge it, and the discipline to adjust it.

Chapter 3 – pick an idea that matters

Charlie suggests doing some inner soul searching here to find what really matters to you. Some practices – trying out mind mapping, asking some questions to challenge our head trash and doubts as well as thrashing, and avoiding creative constipation.

Creative constipation is defined as having a ton of creative projects that keep piling up, but that we cannot finish. This leads to just like human nature, where it becomes uncomfortable. Charlie points out that there is a known tradition that links creativity and destruction: the same energy that fuels creation also fuels destruction. We must be aware of this and funnel that energy in the right direction.

Charlie also puts failure in a new light – its a learning mechanism.

Displacement is your friend

To make room for your best work projects, you must displace other lower level work. This means, saying no to projects. Saying no to other peoples projects that dont mean much to you or aren’t backed by purpose. Pointing out here, to trade up, you have to let go. By holding on to one thing, you cannot take another.

Charlie gives some great exercises here to find out what means the most to you, some steps that you can take to identify what the best work project really is.

Part 2 – Planning your project

Chapter 4 – Convert your idea into a project

Charlie reminds us of SMART goals – which are simple, meaningful, actionable, realistic, and trackable. He gives some questions here on how to measure each of these. There are also some steps to help make the goals more SMARTy.

Charlie also asks us to mark each project with levels of success, being it small, medium, or large. By identifying it up front, we can avoid beating ourselves up when a goal doesn’t meet our expectations. We are laying out the expectations up front so to not be tricked later.

No date = No finish

Success pack

Gather a group of people who will support you along your best work projects. Turn to them when you need help, guidance. These can be mentors, but not necessarily there with you. They can be like in the book “Think and Grow Rich”, where you could ask yourself what that person would do, even when they are not physically there or available for a call.

Chapter 5 – Make space for your project

Charlie stresses that there is no time unless you make it. If your project is important, you will find a way to block up times in your day to focus on it.

Some steps:

  • Chunking
  • Linking
  • Sequencing

By doing these steps, we can create a plan to make space for the project.

Finding the goal of this chapter is that it’s a marathon, not a sprint. Plan the sprints to be only three focus blocks per week to maintain momentum, efficiency, and focus.

Think of the chunks of work over time as blocks. You can have so many blocks per week.

The project pyramid. Made of Yearly Goal at the top, quarters, months, then weeks.

There are blocks of time to schedule, based on some categories:

  • Focus Blocks
  • Social Blocks
  • Admin Blocks
  • Recovery Blocks

The 5 projects rule

Charlie states that the human mind can at best focus on 5 projects. Any more and we will thrash more, as it takes 16 minutes to refocus on a task from interruption or refocusing on a new task type.

Charlie also reminds us to make time for recovery, as we’re in this for a marathon, not a sprint.

3 focus blocks per week

By only having three focus blocks per week per project, we avoid ‘thrash crash’, which is the price we pay for bouncing between projects and refocusing. Try to be aware of this and plan accordingly.

Chapter 6 – Build your project road map

Finding your true flow – Gates

Focus on your strengths, use them to your advantage. Use this gage to find your strengths:

  • Genius – what seems to be an expression of an inner creative force
  • Affinities – what you’re drawn to
  • Talents – what seems to be your native skills or capabilities
  • Expertise – What you’ve learned through experience and practice
  • Strengths – What seems to come easy for you

Charlie here calls our Jonathan Fields and his Sparketypes that can help guide along your strengths. Charlie also calls for a budget that you can use to support yourself along your best work projects. By spending some money on yourself, within budget, you can buy more time to work on your best work projects. The example he gives here is brilliant – paying for grocery delivery service if it takes time away from your project during your highly creative times.

Shared mental models

Charlie gives some symbological meanings to completing by giving some simple mental models. It’s not really the ideas here that are original, but rather the ideas with their corresponding mental models that make this book shine.

Head Trash

For example, I catch myself sabotoging my own projects, ideas, or thoughts. The mental model i’ve had before has been ‘what I say when I talk to myself’, Charlie calls this ‘head trash’. The symbology there is powerful – trash being something that is stinky and we don’t need to keep around but we keep around in our heads.

Charlie then attacks the more important questions that revolve around momento mori – that you have only so many ‘best work’ ideas left in your life. This number is found by taking 85, subtracting your age, and dividing by 5 and rounding down. This time for projects

Creative constipation

Another great mental model is one of ‘creative constipation’. In that, when we have a fun creative idea, we may not act on it. And all humans have experience with constipation, it’s very uncomfortable. Charlie addresses this again by stating, by finishing one, we can move on to the next. However, if we start, and perhaps do not finish, it will build up to those uncomfortable levels.

Success Pack

This is the idea that with it takes a village to raise a kid. Like the kid, the project too needs champions that can help keep you on the path to success.

Chapter 7 – Keep flying by accounting for drag points

The mental model here is that engineers need to account for drag the more and more velocity they are moving at. The same thing works here for projects, be aware of it. The person most guilty of adding drag to your project is you.

There are some no-win stories you tell yourself.


We tell ourselves myths about success, like it will wreck or prevent a relationship, the success vs virtue myth, and the ‘what if i cant do it again’ myth. These are all false. Many can go on to create success without any bad effects, as long as one plans the blocks appropriately.


We often choose mediocrity in the short term, because we don’t want to succeed due to the no-win myths above. But we also don’t want to fail – mediocrity is the space between success and failure.


OPP = other peoples priorities. This can take you away from your best work. Learn how to get away from them. The longer your best work project goes on, the more OPP you’ll have to contend with it. Plan ahead that you need to respond to them. If you aren’t clear about your priorities, you’ll continually be beset with OPP.

Look for opportunities that you can include OPP into your own work, somehow.

Derailers and Naysayers

There will always exist some that will take you off your project and into doubt. Derailers might now know that they are derailing you. Tell them or get curious to see why they do that.

Naysayers are just that, haters are going to hate. Avoid them. Or instead, turn to your success pack.

Charlie says:

Every ounce of energy you use grappling with a naysayer is much better spent on working on your project and interacting with your success pack

Project post-mortems

Take some time during a project to do a post-mortem. This isn’t to say the project will die, but look for opportunities to improve. Of course, you can also benefit by attempting to think through these things from the start, of course. Attempt to do as much learning as you can.

Part 3 – Working the Plan

Chapter 8 – weave your project into your schedule

Basic rules

The weekly block schedule, the Five projects rule, and your project road map together create a plan that you can follow and space to do the work.

Momentum planning is Charlie’s term for the continual process of making and adjusting plans across all time perspectives. This means, doing weekly reviews, morning planning, and triaging. This also means weaving in the time blocking, project pyramid, and the Five Projects rule.

Make sure your environment is working for you

The environment can define the working conditions. Charlie gives an example of how during his graduate school time, most of his best writing happened in 6 years over about 60 days. This was because he tackled writing at the library.

The environment you work in is very important – providing for your focus, momentum, and creativity.

Stacking and Batching

Charlie makes the good point that it takes 16 minutes to refocus after being pulled from focus. There are some tricks he suggested, calling them stacking and batching.

Stacking = doing multiple things at once, when concentration is not required. The example here, while doing laundry, listen to an audiobook. While it seems like it’s multitasking, it’s not. Due to the less needs of the cognitive side of the brain, this becomes easy to do, riding the muscle memory train. Other examples: doing a meeting over a hike, exercising in the park while with the kids.

The second is batching – the example being that you set up admin blocks (described before) to check email, do your paperwork, etc. Batch them up together to tackle in one go around.

Reducing the dread-to-work ratio

Referencing the famous Mark Twain comment of eating a frog in the morning. Do it as early as possible, so that the rest of the day does not sap your creative and cognitive functions, while also decreasing the dread-to-work ratio of your day.

Dread is a function of time, meaning that if a chunk of work takes 5 minutes, it still takes 5 minutes. However, the ‘dread’ increases substantially with time. The longer it sits there, the more dread you’ve invested into the task. It’s the psychological size that haunts you more than the task at hand.

Charlie states that the time you dread the task itself, the distinction becomes blurred, to the point that the time you spend worrying or thinking about it could have spent doing other things. If possible, batch the frogs together.

However, not all frogs can be done early in the morning, as they may require focus blocks. There will always be frogs, it’s best to address them for what they are and set up some time to get them done.

5 / 10 / 15 split

This little time split reminds you to keep 5 projects at max, with 10 minutes for momentum planning before you start your day, and 15 minutes at the end of your day. This keeps you focused on the daily level.

Try to not plan too far out ahead, the example being you do not plan every gas break, stop light, and every other part of your travel if you are taking a car trip.

Chapter 9 – Build Daily Momentum

Make sure you celebrate small wins. Lean more on your success pack to help you identify wins.

Remember that great is the enemy of done. The more you care about the project, the less ‘done’ it can achieve.

Create a win journal and store small wins there. The more small wins you get, the more momentum it builds. The more small wins, the better the big win will become.

Create routines and habits that make it easier to build and maintain momentum.

Charlie also suggests leaving a ‘bread crumb’ trail, which will help you pick back up on projects when you leave them for a bit.

Charlie also addresses some tips you can use to avoid distractions:

  • Use dumb tech
  • Turn off notifications
  • Delete apps or remove capabilities
  • Lock yourself out – Mac has Cold Turkey blocker, for example
  • Create better defaults during transition periods to replace the distracting defaults you may have

Cascades, tarpits, and logjams

This is a nice mental model he shares – cascades are when one project gets behind, it cascades down. Tarpits are when you leave a project for so long, that when you come back to it, it’s stuck in a tar pit and hard to get out. Log jams are what happen when you have too many projects and they get jammed and stuck all at once. Avoid these by the 5 project rule, leaving bread crumbs, and planning appropriately.

Chapter 10 – Finish Strong

Know that by finsihing one project, you are not done. There is more work to be done. It never ends. However, when you finish one project, make sure you take a victory lap and celebrate the win. Lean into your success pack to help drive this.

CAT work

CAT = clean up, archive, trash

This is the process you take between projects to clean up any artifacts, archive all the things before, and trash what you no longer need. If you don’t do this between projects, you may waste time in the middle of a project doing these. That becomes a distraction.

After action reviews

In agile land, these are basically retrospections. Take time to ask the questions to improve later.

  • What went well?
  • What setbacks, challenges, or missteps did I experience?
  • What did I learn?
  • What habits, practices, or routines do I want to keep doing going forward?
  • Were there any especially important difference makers to the project?

However, one thing is important here. Finishing a best-work project unlocks new realities. Embrace them.