PDF Summary:Start Finishing, by Charlie Gilkey

For too many of us, big ideas stay in our heads or our notebooks and never become reality. In Start Finishing, productivity expert Charlie Gilkey teaches you how to finally do the things you’ve always imagined. He provides practical frameworks to help you overcome procrastination, work through psychological barriers, and focus your efforts on purposeful, meaningful work.

In this guide, we’ll explain Gilkey’s definition of a project and why designing and committing to a project is a fundamental step toward achieving your goals. We’ll then explore how you can make the most of your resources and work them into a realistic plan of action. Finally, we’ll discuss how to wrap up a major project and get ready to move on to your next important goal.

Our commentary will give specific ideas to turn your dreams into reality. We’ll also compare this book with other productivity guides, such as Feel-Good Productivity. Finally, we’ll explore research from psychology that supports Gilkey’s main principles.

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Planning Your Project

Now that you’ve learned about authentic projects and the importance of fully committing to one, we’ll discuss Gilkey’s approach to project planning. He emphasizes two elements for this planning stage: making the most of limited resources, and developing a realistic plan with a reasonable deadline.

Make the Most of Your Resources

Recall that a lack of resources was one of the five common barriers to completing a project. It’s also the only barrier that’s rooted in physical and logistical limitations as well as psychological ones.

However, Gilkey says that you probably have more resources at your disposal than you think. Therefore, overcoming this barrier is a matter of finding the right people to support you, and spending your project’s budget—however large or small it is—where that money will have the greatest impact.

Make the Most of Your People

Gilkey says there are four kinds of people who will naturally want to support you as you work on an authentic project. Finding people from these four categories will enable you to create an effective team to boost your productivity, as well as providing you with the support and motivation you need to see your project through.

The four types of people Gilkey urges you to find are:

1. Mentors: People who have already done what you’re trying to do, or something similar. They have experience and knowledge that you lack, so they can provide useful guidance to help you avoid pitfalls and achieve your goals. While professional advisers and coaches will expect to be paid for their services, you can often find people who are happy to share their insights for free.

(Shortform note: Older people are often happy to share their skills and knowledge with those who are less experienced than they are. In From Strength to Strength, management expert Arthur Brooks argues that this is because our creativity and energy decline as we age, but our wisdom and accumulated knowledge continue to grow. Therefore, older people—who might be frustrated by the decline of their own professional skills—tend to embrace opportunities to be useful by teaching or guiding others.)

2. Colleagues: People at roughly your level of experience and skill who are willing to collaborate with you on your project. Aside from helping you with the actual work, such people should also be willing to challenge your ideas and point out your mistakes when necessary. Note that you don’t necessarily have to pay colleagues to get their support; it’s likely they’re working on authentic projects of their own and will be open to exchanging their help for yours.

3. Advocates: People who may not have the skills to directly help with your project, but support you in other important ways. Family members and close friends will often act as advocates—for instance, by offering encouragement and emotional support, helping with day-to-day chores so that you can focus on your work, or lending you money if you need it.

(Shortform note: One of the simplest, yet most effective things colleagues and advocates can do is hold you accountable through specific commitments and regular check-ins. A study by the American Society of Training and Development (ASTD) supports this idea. The ASTD concluded that, if you simply have a goal in mind, you only have about a 10% chance of achieving it. However, if you make a commitment to someone else, your chances of reaching that goal increase to around 65%—and if you schedule regular check-ins with that person to hold yourself accountable, your odds go up to 95%.)

4. Beneficiaries: People who stand to benefit from your project. For example, if you want to create a crew of volunteers to keep the neighborhood clean, then the people who live there are the beneficiaries; if you want to open a business or create a new product, then the people in your target audience are the beneficiaries. Because they benefit from your success, these people may be more likely to help you.

(Shortform note: It may seem odd to insist that an authentic project—something meant to be important and fulfilling to you personally—must have beneficiaries. However, psychology offers one possible explanation: Doing work that benefits others is necessary in order to feel fulfilled. In The Courage to Be Happy, Ichiro Kishimi and Fumitake Koga (citing the work of psychologist Alfred Adler) say that helping others is a fundamental part of feeling welcomed and valued in your community. Those feelings of belonging and worth, in turn, are necessary for your personal health and happiness. In short, although it’s counterintuitive, they argue that the way to make yourself happy is to help make other people happy.)

Make the Most of Your Money

Budgeting is a crucial element of project planning. Gilkey argues that almost all projects require some degree of investment—even if it’s just to buy the supplies you need—so it’s important to set a budget and keep those expenses under control.

The author encourages you to view budgeting as a useful boundary-setting exercise rather than as a restrictive constraint. The goal isn’t just to limit your spending, but for you to strategically use your resources so you can get the best returns on your investments.

For example, instead of hiring a babysitter to watch your children while you work on this project, perhaps you could arrange with some friends to take turns watching each others’ kids for free. You could then use the money you save for something directly related to your project, like upgrading your computer or hiring an assistant.

Setting a Reasonable Project Budget

It can be difficult to come up with an accurate budget, especially if you don’t have any experience as a project manager. One method for creating a budget is the three-point estimation technique, which allows you to cover a wide range of possibilities.

This approach involves coming up with three different estimates. The optimistic estimate is how much time and work—and therefore cost—the project will involve if everything goes well. The pessimistic estimate is how much the project will cost if everything that could reasonably go wrong does. Finally, the most likely estimate is exactly what the name suggests: your best guess at how much the project will cost, based on what problems you might encounter and how likely each of those problems is. You can then set your actual project budget by simply taking the average of those three estimates.

While the three-point estimation is designed to help you hope for the best and prepare for the worst, many experts recommend setting aside an additional 5% to 10% of your budget for emergencies. While the estimation will help you prepare for any scenario you can predict, this contingency fund will help you deal with expenses and setbacks you couldn’t predict.

Design a Realistic Plan

Gilkey stresses the importance of making a detailed and specific plan for tackling each of your projects. By doing so, you turn vague to-do lists into concrete timelines, which will provide much-needed guidance and support as you work toward your goals.

Step 1: Break Down the Project and Arrange the Pieces

Gilkey’s first step toward making a realistic plan is to break the project down into tasks or groups of tasks that will carry you from your starting point to your goal. You may also find that those tasks can, themselves, break down into smaller tasks, so get as specific as you need to during this step. Aside from enabling you to turn a goal into a plan, this process will give you a more accurate idea of how much time and work your project is likely to take.

Once you’ve identified the individual pieces of your project, you can determine how they connect: which tasks have to be handled first, what those tasks enable you to do next, and so on. By arranging and connecting the pieces in this way, you’ll be able to come up with a logical action plan to carry you from your starting point to your goal.

Deconstructing a Project

Beyond improving your time and cost estimates, breaking down a project as Gilkey suggests can enhance accountability among your team members (if you’re working on a team project). This is because it allows you to assign specific tasks to specific people, with reasonable deadlines for each.

This strategy also helps protect you from scope creep, a situation where your project’s needs (and therefore costs) expand beyond what you predicted and budgeted for. Clearly defining and laying out each task ahead of time helps you avoid that pitfall—you’ve already planned out how you’ll get from the project’s starting point to its endpoint, so it’s unlikely that you’ll need to put in a lot of unexpected work or money.

However, Gilkey’s method does run the risk of overplanning. In other words, breaking down a project too far can lead to a rigid plan, making it difficult to adapt to unexpected problems or take advantage of new opportunities.

Step 2: Make a Realistic Timeline

The author challenges the common approach of starting with a deadline, then working backward to create a plan. He argues that you’ll get more realistic timelines by planning based on your actual work capacity, meaning the amount of work you (and your team, if applicable) can realistically and consistently get done. In short, he argues that it makes more sense to create a deadline based on your plan, as opposed to creating a plan based on your deadline.

(Shortform note: When making a project timeline, consider how many productive hours of work the average person can put in each week. This will vary depending on the individual and the type of work they’re doing, but research has provided a couple of useful benchmarks: You’ll see greatly diminishing returns after working more than 45 hours in a week and the maximum number of productive hours for the average person is around 55 per week. Any time beyond that 55-hour benchmark doesn’t result in more work getting done, because the worker is too exhausted to be productive.)

Gilkey also notes that projects involving more than one person will inherently have periods of downtime, and people often overlook this fact while planning. This commonly happens when team members can’t start their work until other team members finish theirs—for instance, an editor can’t do their work until a writer gives them something to edit.

So, while creating your timeline, try to anticipate these transition periods and bottlenecks. However, the author says you should also be prepared to adjust your plan and push back your deadline as issues like this arise.

(Shortform note: As risk analyst Nassim Nicholas Taleb notes in Antifragile, predicting the future—such as estimating how long a project will take to finish—is practically impossible. Furthermore, predictions become less accurate the farther into the future they go and the more variables they have to contend with. Therefore, a long-term project involving multiple people is practically guaranteed to run into delays and problems that you weren’t able to predict. Taleb’s suggestion is to prioritize adaptability over efficiency. In other words: Keep your options open and be ready to adjust as the situation changes, rather than locking yourself into an idealized plan that assumes everything will go smoothly. This echoes Gilkey’s advice to be prepared to push back deadlines as problems arise.)

What to Do After You’re Done

So far we’ve gone over the importance of turning a dream into a project, as well as a realistic approach for doing so. In this final section we’ll discuss Gilkey’s advice for what to do after completing an authentic project: Tidy up your physical, mental, and digital workspaces; review your performance to find ways you can do even better on your next project; and take care of yourself by celebrating and resting.

Clean Up After Yourself

Gilkey says that even after your project is finished, there will be loose ends and “junk”—both physical and emotional—to tidy up. Doing this cleanup work ensures that you and your team can keep operating at peak performance in the future, rather than having to work around the remnants of old projects.

The most straightforward type of cleanup work (and often the easiest, though that depends on the type of project) is tidying up your physical workspace. This includes things like sweeping, throwing away trash, making sure your tools and equipment are clean and organized, and so on. In short, do whatever must be done to ensure that your workspace is ready for the next time you need it.

(Shortform note: In The Life Changing Magic of Tidying Up, Marie Kondo says that it’s tempting to completely clean one room at a time, but it’s actually more efficient to clean by category rather than by area. This means going through your entire workspace and gathering everything from a particular category (say, tools) into a single place, like a large table. You can then examine each individual item to decide whether you want to keep it, and if so, where to put it. Note that Kondo wrote this book to help people tidy their homes, so her specific categories—clothes, books, papers, miscellany, and mementos—may not apply to your workplace. However, the general principle of cleaning by category rather than by room still holds.)

Along with cleaning and organizing your physical workspace, the author urges you to tidy up your digital workspace in the same way. This means organizing documents into clearly labeled folders, deleting duplicates and outdated versions of files, and making sure all of your documentation and notes are easily accessible in case you need to refer back to them.

(Shortform note: Psychologists say that clutter (both physical and digital) isn’t just inefficient, it’s also harmful to your mental health. First of all, messy spaces are stressful and distracting—being surrounded by too many objects can overstimulate your brain, which tires you out and makes it hard to stay focused. Secondly, clutter makes it more difficult to find what you need, which can turn even simple tasks into frustrating ordeals. Finally, clutter often sparks feelings of shame—your home and workspace are “supposed” to be tidy, so the clutter feels like a constant reminder that you aren’t living up to that standard.)

Finally, Gilkey says that you’ll most likely also have some social cleanup to do after a project. This often involves following up on past conversations, fulfilling promises and obligations that you’ve made, and addressing any interpersonal problems that emerged during the project. This is important because any lingering resentments that team members have (toward each other or toward you) will become emotional “clutter,” hindering future work as surely as a workspace filled with physical clutter would.

(Shortform note: The Zeigarnik Effect in psychology is one explanation for the emotional clutter Gilkey describes. This is a phenomenon where people remember uncompleted or interrupted tasks more readily than completed ones, and they feel compelled to seek closure by finishing those tasks. However, the Zeigarnik Effect also applies to interpersonal relationships, causing people to ruminate on their “unfinished business” with one another—in other words, their resentments toward each other. In a work environment, that unresolved tension can be a major distraction, as well as interfering with people’s ability to work as a team. Therefore, doing social cleanup like Gilkey suggests can help you avoid such issues going forward.)

Review Your Work

Before putting away a project for good, Gilkey urges you to take time to critically examine the project as a whole and your performance during it. This process of reflecting on your work helps turn those individual experiences into personal development. That development, in turn, will help make your next project even more successful.

He models this principle on the After-Action Reviews (AARs) used in the military. The AAR process involves asking clear and specific questions about what you just went through. For example: What parts this project went well? What changes did you need to make along the way? What new skills or knowledge did you gain? What habits and practices were particularly effective?

How to Do an AAR

Contrary to what Gilkey writes here, an effective AAR is not simply a series of questions and answers. Rather, it’s an active discussion involving the entire team, centered around four specific questions:

1. What did we plan to do?

2. What did we actually do?

3. For any instances where we diverged from the plan: Why did that happen?

4. How will we achieve a better outcome next time? Alternatively, how will we repeat this success?

The discussion aspect of an AAR is crucial for gaining insight and finding opportunities for improvement. Simply having your team members answer the questions individually isn’t nearly as effective because there’s no opportunity for them to challenge each other and refine their ideas.

Celebrate and Rest

Finally, don’t overlook your needs. Gilkey says that you’re going to need to do two things after completing a difficult and stressful project: celebrate and rest.

Many people feel uncomfortable with openly celebrating their accomplishments, viewing it as boastful or unnecessary, but Gilkey argues that it’s an essential part of an authentic project. This is because a celebration isn’t just about recognizing your achievements, it’s also a chance to acknowledge the community that supported your project. Sharing your success strengthens your connections with your team and your supporters, and it can also serve as an inspiration to others. The author adds that a celebration can be as large or as small as seems appropriate: anything from sending a simple text message thanking everyone involved to throwing an actual party.

(Shortform note: Celebrating successes is one of the most effective ways to keep yourself and others motivated for future achievements. In The Molecule of More, the authors offer one explanation for why it’s such an effective practice: Making progress toward a goal causes your brain to produce a chemical called dopamine, which causes intense feelings of pleasure. Because the dopamine high is so enjoyable, it naturally motivates you to keep working toward your goals in order to recapture those good feelings.)

However, alongside the celebration, Gilkey says that transitioning between projects requires rest and reflection. This is especially true after finishing the intensely personal work involved in an authentic project. Take whatever time you need to recover from your hard work (both physically and emotionally), address any personal tasks you’ve been neglecting, and mentally prepare yourself for future endeavors.

(Shortform note: Rest isn’t just about taking time away from work—it’s also important to make sure you rest in a way that’s truly restorative. In Willpower Doesn’t Work, psychologist Benjamin Hardy says you can accomplish this by designing an environment that encourages rest and shields you from outside stressors. Some of his suggestions include decorating your resting space with art that helps you feel calm or uplifted, bringing in personal items that make you happy, and getting comfortable furniture to help you relax.)