This is the fourth in a series of posts about travel, work, and living on your own terms. You might want to start here: A Radically Different Life, You Are A Product: Defining Your Vision, and You Are A Product: Core Values.

Setting and reaching goals is my favorite thing to do. That’s probably a weird thing to say, but I’ve done it forever and even built an entire site around it. I like holding myself accountable and being able to look back to see what I’ve been able to achieve. Half of the “cool” — or sometimes just practical — stuff I’ve done in the last seven or eight years was because I put it on my list of goals and kept hacking away at it until I made it so.

Some were easier than others, but setting goal posts for myself has been the best way to stay motivated even when other things go haywire. (Looking at you, student loans.) Sometimes they took years longer than I thought it would, but when I finally got to check them off, it was like younger me saying “See! I knew you’d get there some day 👏 .”

I used to set 101 goals for myself every year. It’s how my whole goal-smashing journey began. It was the first hint at this weird life-hacking, lifestyle design, whatever-you-want-to-call-it habit I ended up cultivating.

As it turns out, they were just the start of my personal KPIs.

One of the key tasks of product development is breaking down problems and goals into achievable bits that can be executed and measured to move the company toward its vision. The company has established where it needs to go. Now: How does it get there?

Products are pulled in a thousand different directions at any given time. There are customer support issues, there are bugs in the software, there are market demands or partnerships or, sometimes, Shiny Object Syndrome — some glorious new idea that for sure will make the company MILLIONS. Often it comes down to the product people to weigh these shiny new ideas and make sure the product is staying on track.

The easiest way to do this is to have a defined set of tasks that move the company toward its goal and prioritize them in a way that makes it very clear what’s at stake if something shiny gets in the way. By saying “this is what the company is working on right now and here’s where it will get us,” the company can weigh any potential distractions against that list and say “is this distraction worth it?”

That’s certainly how I manage my own Shiny Object Syndrome.

I take my vision and figure out what’s standing in my way. I break those things down into concrete tasks that bit by bit will chip away at my goals. I keep those tasks prioritized and very clear so that when, inevitably, something interesting comes along that might distract me from my tasks, I can say “NO! Go away, shiny object! Your kind isn’t welcomed here!” and move on with my life.

Case in point: My major goal for this year is to travel as much as possible while working remotely. To make it even more measurable (and fun!), I have a goal of traveling to 30 countries before I turn 30 in October. It’s been going well so far.

A few weeks ago, I was poking around on Redfin looking at real estate in this one town I’ve been following. It’s been experiencing a bit of a renaissance and I’ve been debating if I want to buy a place there as my home base. I know I want to have a place of my own in the next few years, but it was never on the docket for 2016.

As you would expect, given my Shiny Object Syndrome, I found a place that fit the bill and went to look at it. Thus began a week-long distraction from my goal. I knew full well that buying this place would mean I wouldn’t be able to travel for almost the rest of the year. It would almost certainly mean giving up on my #30Before30 goal.

Yet I still considered it. It would be a good investment. I even went as far as talking to a mortgage broker and starting to line up my financial ducks. It seemed like the wise choice to make. I could rent it out while I travel, I could X, Y, Z. I rationalized it all day and all night. But something was still tugging at me. It meant not reaching the ONE main goal I set for myself this year.

Is that something I was willing to sacrifice?

No. It wasn’t.

So I let the place go. I may end up regretting the decision in five years, or it may end up being exactly what needed to happen. Who knows, maybe stars will align and after I finish my #30Before30 it will still be available and I’ll re-consider it then.

But it was as close call.

When developing a product strategy, once a company has its vision defined, it’s time to figure out three key things:

  1. What’s standing between their current business and reaching their vision?
  2. What do they have to work with to help bridge that gap?
  3. Of those hurdles, which are the most important ones to address right now and what can wait until later?

By understanding the hurdles in its path and the tools the business has in its belt to help tackle them, it can figure out a plan to take them down one-by-one.

Most businesses go through exercises like this annually, quarterly, and, in some cases, every few weeks when reviewing a sprint.

When eating an elephant take one bite at a time — Creighton Abrams

Developing the ability to break down big problems into bite-sized chunks that you can reasonably achieve given the resources you have at your disposal makes climbing that big mountain toward your vision so much more manageable.

This is actually the thing I do most often in my personal and professional life. It’s one of my favorite things to do because it feels like a superpower.

“That thing that sounds big and complex and really hard to do? If I deal with X then Y then Z then A then B then C, before I know it I’ll be at the promised land?” It sounds like magic.

Of course there’s no guarantee that it will work out, because life, and randomness, and other factors, but that’s a topic for another day. The point of this exercise is to break down the intimidation and fear that comes with starting to tackle some big, scary goal.

Now is when we get down to brass tacks and turn our vision into the steps it will take to get there. Time to get tactical.

What’s standing between me and my vision?

The first task in this exercise is to figure out what’s in your way: Your blockers. Again, I typically go to my trusty notebook and, in complete stream of consciousness, write down anything I think I have to address in order to reach my vision.

It could be logistical challenges (like time or money), it could be knowledge gaps (I need to learn something specific before I can do it), or it could just be feelings I have about it (It’ll put me really out of my comfort zone or I’m scared of heights, etc.)

It’s OK to be a bit skeptical and negative at this point. It’s better to know what might come your way so you can be ready to adapt.

What do I have to work with to help bridge that gap?

This part is always the toughest for me. It involves thinking about everything I have going for me. What’s in my favor as I try to reach my vision? It’s kind of the antithesis of being humble, but that’s ok. This is just between me and my notebook.

I usually start with myself and work outward. I list the particular skills that might help me along the way. I list the experience I have that might be relevant. Sometimes I list the skills that don’t seem relevant at first but might be adaptable to my goal. This piece involves a fair bit of self-awareness. It also might help to ask friends and family if you get stuck.

Once I’ve established what my personal resources are, I expand out to the people and conditions around me. I list friends and acquaintances that might have done something similar before or may have all sorts of useful tips and advice. I also take into account whether external factors may be in my favor like a huge trend toward the thing I want to do or a new technology came out that will make it easier for me to do what I want to do, or even more simply, a book on the topic that I can read!

In the end I have a rough list of blockers — the things that I anticipate needing to overcome to reach my goal, and a list of of resources that I can tap into to help me reach my vision if needed. Next up is putting some structure around it.

The toughest part of day-to-day product development is prioritizing what to work on first. Everyone at the company has grand ideas about what will make a big difference, but there are only so many things they can do at once. This is where figuring out what the company should focus on and in what order becomes key.

There are about whole pages of Google results promoting different ways to go about determining the priority of a set of goals or tasks in product development, but they all have the same basic output: figuring out which item will get the company the most bang for its buck. Which will have the greatest impact with the least amount of effort? Or, if it is a great effort, does the impact outweigh the drain on resources?

We need to do the same when setting our personal goals.

Assessing Blockers

The list of hurdles essentially functions as mini-visions or themes that you need to address to reach your goal. As normal humans with 24 hours in our day, we can only work on so many of them at once, so we need to pick which ones are the most important right now and which ones we can put off until later. In product development, we call these blockers.

In your list of blockers there’s a good chance one or two of them isn’t actually a blocker. Don’t worry, those pesky fake blockers always sneak their way into the lists of even the most experienced product people. Let’s sort them out first. The MoSCoW method is a quick and dirty way to filter out the cruft. Basically, you sort your blockers into “must deal with,” “should deal with,” “could deal with,” and “won’t deal with.” The sneaky non-blockers are in your “won’t” list. You can chuck those aside for now.

The ones to focus on now are in your Must and Should lists. Depending on the number, you can probably break that down some more. Try prioritizing them yourself from most important to least important, but if you need something to help with the decisions, a bang for buck matrix will help:

impact vs difficulty

Clearly, I won’t be a professional doodler any time soon.

Plot your blockers where you think they belong along the impact and difficulty axes. Focus on the high impact first. If it’s low impact and low difficulty, ask yourself if it’s even necessary. If it’s high impact and low difficultly, that should almost definitely be one of your first orders of business: it’s an easy win!

I’ll be honest with you, I don’t use these techniques very often outside of work because, at this point, I’ve basically trained my brain to think of everything this way, so however you get to your prioritized list: Awesome! Just make sure you have one.

Now we know what we’re working with!

With two or three mini-visions to focus on for the next few months, we have to do the work of breaking those down into actual tasks. I like working in 1, 3, and 6 month chunks so that the timeframes are manageable and measurable. The breakdown of each mini-vision is actually fairly straightforward: It’s the same exact exercise we just did to determine our blockers and resources at a smaller scale! Funny how these things work.

In the end, you should end up with a (SMART) list that’s something like:

  1. Put $100 toward this goal into a special savings account every month.
  2. Read This Useful Book by August 1st.
  3. Set up chats with Person X, Y, and Z to get advice on Something Specific About My Vision for July.
  4. Research this Very Relevant Topic.
  5. Spend 20 minutes doing This Useful Thing.
  6. etc.

This all gets much easier and much quicker with practice. With 8 years of goal setting and prioritizing under my belt, I can get to this point in about 20–30 minutes. It’s just a matter of building the habit!

Granted, at an actual company (that hopefully isn’t building a super awesome human as their vision), tasks look a little bit different. They’re mostly about financials or building a certain feature or reaching a certain milestone, but the process they take to break down their vision into achievable bits is the same at the company level as it is for each individual product and each individual task that it takes to build that product. The smaller goals add up to the medium goals which add up to the bigger goals which help them reach their vision.

At a public company, accountability to goals is actually a pretty big deal. If the company doesn’t hit the goals it set for itself, the shareholders will be pretty disappointed and their stock prices will fall.

Luckily you’re not a public company. But you do have to be accountable to yourself!

These are your marching orders for the next few months. Put these tasks somewhere that you’ll see them and be reminded to do them. Next week’s post (spoiler alert!) will be about assessing your progress and reacting to changes. These are the things you’ll be measuring your progress against. Making these a priority means making your vision just that much more possible.

Time to get started!

What are some of your goals for the next few months? Share it with me on Twitter @jennjenn (or, even better, post them on Betterlist!). If you liked this post, please 💚 it and share it with one of your favorite people. I’ll be posting the next installment soon, so follow along!