Field Reports: Plan Your Week Like a Start-Up Executive

Tyler’s Note:  This is a Riskologist Field Report by Ryan J. Ferrier of Bootstrap My Life. Field Reports are written by readers just like you, so be nice, enjoy the story, and take action on the lesson. To contribute your own Field Report, go here.

I’m a dreamer.

I love to envision the future, what it could be and what it might mean. And normally, the vision is grand.

I’m not, by nature at least, a planner.

A general vision excites me. Specific plans scare me. In fact, just thinking about planning used to paralyze me with fear.

Then I fell into a job at a start-up as an executive assistant—a job that’s nothing but planning and logistics.

I was terrified. Still, I wasn’t about to let this opportunity pass me by. You see, I was dead broke and needed the job.

Failure was not an option.

Planning Can Be Learned

In my new job as a “planner,” I spent the first few months running around like a mad man, feverishly trying to keep up with all the requests that came my way.

My hustle was admirable. My execution, though, was fair at best. I screwed up schedules, forgot appointments and lost documents.

After mastering the art of apologizing, I realized I needed a new approach before I collapsed with exhaustion or got fired.

A friend recommended Getting Things Done by David Allen. For the first time, I saw the light. I didn’t need to work harder, I needed to work smarter.

I needed to put simple systems in place, and let the systems ensure that everything went according to plan.

Quickly, I became known as the get-sh*t-done, planning guy. And boy, did it pay off to get good at planning.

First, I was promoted to a management position. Then, two of my coworkers invited me to join them in starting a gaming company and serve as COO.

I was now Chief Planning Guy. We grew that company to 40+ people and ultimately sold it to Zynga (The company that makes Facebook games), with me handling all the planning and logistics. What?!

Needless to say, I was convinced by the power of planning.

You Can Plan, too… With a Weekly Review!

My hunch is that if you’re reading this, you’re also a dreamer. Maybe you even have a clear vision of what you want your life to look like.

It’s easy, though, to get stuck trying to tie that vision to your present reality.

Planning can help.

During my start-up days, the backbone of my planning strategy was my Weekly Review—time that I set aside to make sure my big dreams are becoming concrete realities.

And it’s not just for corporate types.

I’ve since left my operational role in the start-up world to work for myself, coaching people in career transition. My weekly review remains the key component of my planning strategy.

It’s a 5 step process that starts with a vision (dreams) and plans that vision into actual time slots on your calendar (reality).

I share my process here in the hopes that it might help other dreamers as it’s helped me.

The Anatomy of a Weekly Review

My weekly review takes about 90 minutes, though I usually schedule it for 2 hours. It’s broken into the following 5 sections:

  • Vision (10 mins)
  • Goals (10 mins)
  • Metrics (20 mins)
  • Learnings (20 mins)
  • Planning (30 mins)

Each of these sections answers a single question:

  • Vision. Where do I want to go?
  • Goals. What are some milestones along the way?
  • Metrics.  Am I trending toward those milestones?
  • Learnings. Do I need to adjust my approach?
  • Planning. What’s my next step?

Let’s take a look at each section.


During this time, I take a deep breath, clear away all distractions, and then pull out a piece of paper on which I have my Vision Statement for this year written out. It’s a page and a half description of what I’d like this year to look like.

I then read my vision statement out loud and really try to internalize this picture (sounds hokey but it helps).

Here are some snippets from that Vision Statement:

  • I will be connected to other bloggers and online figures who I can learn from.
  • I will have 500 true fans who have received measurable benefit from my work and actively promote it to others.
  • I will leave the year more motivated, more energetic, and more healthy than I entered it

This practice reminds me that all the administrative work I’m about to do is for a bigger cause. It engages my heart as my hands get ready to execute.

If you don’t have a Vision Statement for what you’d like the year to look like, start by simply writing out three concrete realities that you’d like to see in your life.


Next, I review my goals. I also keep them written out on a single sheet of paper.

I like to create just a few, really simple goals on a quarterly basis. You may want to have just one goal at a time.

My Q1 Goals:

  • Grow my readership by 3x
  • One guest article on a large blog (>5k subscribers)
  • Complete a fully formatted eBook

Here’s a good guide for creating goals.

And here’s a good argument for not having any goals at all.


I then review a few simple metrics for my business. These metrics let me know if I’m on track to reach my goals or if I need to make adjustments.

The metrics I currently track are:

  • Newsletter Subscribers
  • Unique Visitors
  • Pageviews
  • Pageviews per Visit

I log my metrics in my Metrics Dashboard – just a Google Spreadsheet.

Here’s an example of what a simple metrics dashboard can look like.

Your metrics serve as indicators to whether you are on track to reach your goals.

Stay away from over-complicating your life with too many metrics. Just pick a few that are key indicators of your progress.

Also, try to avoid checking in on your metrics too often. It takes time to see trends.


Now it’s time to record learnings from the week. I gather learnings from four major sources:

  • Communication with my readers (emails and blog comments)
  • Clients who I coach 1 on 1
  • Online Communities that I participate in
  • Metrics that I track

Your sources may be very different, but it’s important to identify the places and people in your life that give feedback and input about how you’re living your ideal life.

I record noteworthy learnings in what I call my “Learning Log”. It’s a Google Spreadsheet with a tab for each learning source.

I usually record just small snippets, like:

  • Readers really like career discussion
  • Client X found creating a survey very helpful in job search efforts

If there are things I need to change or implement in the next week as a result of these learnings, then I list those as action items on a single Google Doc entitled “Action Items”.

The items on my “Action Items” list then get scheduled into the following week during the planning section of my review.

The workflow looks like this:


I plan the upcoming week(s) using two tools:

  • My Quarterly Snapshot
  • Google Calendar

My quarterly snapshot is a way for me to take a high level look at major items that are upcoming.

I use it primarily as an editorial calendar for planning what articles I am going to publish on my site and when, but I also record a few other items.

Here’s what the colors represent in the image below.

  • Red  = article on my site
  • Grey = travel
  • Blue = review times
  • Green = birthdays and other important dates

I’ve adapted my quarterly snapshot from Michael Hyatt’s annual time block

After making the necessary adjustments to my Quarterly Snapshot, I then look at my calendar for the next week to see what meetings I already have scheduled.

Finally, I take any items that are on my “Action Items” google doc and schedule a time for them.


The Greatest Dream

Hebrew King, Joseph, was also a dreamer. He dreamt that he was both a sheave of wheat planted in the ground and a star floating in the sky.

I love this picture.

A sheave of wheat only comes about after the soil has been tilled and routinely watered. It takes patience, hard work, and planning.

A star floats effortlessly in the sky shining for all to see.

For us dreamers, it’s a great reminder to put our hand to the plow as we keep our eyes on the stars.

Ryan J. Ferrier helps young people create professional success by developing their personal platform at Bootstrap My Life. You can follow him on twitter at @ryanjferrier.

Image by: katstan