How to set personal goals like successful companies do

Child learning archery.
Reaching your targets is hard.

In 2021, for the first time in 27 years, I will be working for myself. When you work for yourself, you’re basically a company of one, so it makes sense to manage yourself like a business. Here’s how I’m setting and tracking my personal goals this year.

If you read my first post, you know how excited I am about this new direction in life. But excitement is not enough. Even though I have a general sense of direction, there will be times when I lose sight of the path, feel overwhelmed, or just lazy. Without an employer to guide your efforts, a boss to assign you tasks, and colleagues to provide camaraderie, you have to supply these things yourself.

As I faced the transition to self-employment, I asked myself how to avoid these dangers. How can I ensure that I keep moving toward my dream, that every action brings me closer to it, and that I work consistently? Below I describe the system of setting and tracking goals that will keep me going this year.

Let’s start with an overview of some popular goal-setting frameworks.


This is the gold standard for goal-setting. If you’re ever taken a productivity workshop, you’ve likely been taught to make your goals:

  • Specific, so that you know exactly what to do,
  • Measurable, so you can know when you’ve achieved them,
  • Attainable, so it’s not too ambitious,
  • Relevant, so you’re motivated to do it,
  • Time-bound, so you have time pressure and can’t fuck around.

I’ve found this framework very useful over the years. It helps you turn vague aspirations into something concrete that you can pursue.


But if you feel SMART goals are too clinical, here’s an alternative:

  • Dream-driven: your goal should be in line with a greater vision for your life,
  • Uplifting: it should fill you with inspiration and excitement,
  • Method-friendly: you should be able to build habits and practices around it, or it will become a one-off task
  • Behavior-triggered: have something to remind you to chase the goal.

I like this framework for its focus on vision, inspiration, and excitement, as well as habits and systems. This advice is synergistic with Atomic Habits, which I highly recommend.


This is a management framework popularized by Google, who credit it with helping make the company successful. The idea is to set objectives, which are aspirational goals, and key results, which are measurable and specific. Each objective should contain 3-5 key results, that together help bring it about.

OKRs are useful for breaking down the organization’s strategy into specific tasks. As they are public within the company, they help to align individuals’ and teams’ efforts with the company objectives. But in the context of personal goals, this is not important.

I decided to use OKRs for my personal goals this year because they combine the best aspects of SMART and DUMB goals. Key results are specific and measurable, while objectives can be vague, inspirational, and exciting. But in addition to OKRs, in fact above them, there’s a single vision that gives me direction every time I look at it.

The North Star

It’s to never work 9-5 again. To make money doing the things I enjoy and am excited about. To not have to sacrifice my interests to work on a schedule for someone else. To have the freedom to work where, when, and how I want.

These aspirations, distilled into a punchy phrase (never work 9-5 again) sit at the top of my goal hierarchy. Underneath, I have several objectives that define the general framework of action. And each objective has several key results that give me actionable tasks.

Example: my OKRs

Without further ado, here they are:

1. Build an online audience
1.1. Publish 52 blog posts, 500+ words, with a maximum 2-week gap between postsQ43
1.2. Publish 12 book notes on the blog (fiction or non-fiction)Q41
1.3. Publish 10 videos (one per week) at JurekWieQ13
2. Try my hand in business
2.1. Brainstorm 50 project ideas that match my interests and valuesQ116
2.2. Identify 20 trends, markets, or growing industriesQ17
2.3. Test/validate 5 ideasQ40
3. Expand my network
3.1. Reach out to 10 people in my existing network who can be potential partnersQ14
3.2. Meet (have personal chats with) 30 people from entrepreneurship communities or referred by existing acquaintancesQ21
3.3. Reach out (ask for advice) to 10 people I admireQ20

The KRs have a deadline defined by quarter. (Q1 is the end of March etc.) I keep them on a Notion page, where I periodically update their status. Here’s where measurability comes in handy – you can easily see how far you are from achieving each KR.

A few observations:

  1. The business OKRs are vague on purpose. Because I am exploring various avenues for making money, the focus is to find and try out several business ideas. Once I’m working on an idea, I will come up with specific goals for it.
  2. The exploration is why I’m building an online audience and expanding my network. It’s all about being exposed to new people, ideas, and opportunities while building a personal brand.
  3. I expect the goals to change. I originally had an entire objective devoted to writing a novel but decided to deprioritize it, to focus on cash flow first at the expense of passion projects. Likewise, I had a key result about posting on Twitter but I put it on hold until I define a proper strategy for it. I may drop KRs and add new ones: maybe I won’t need to test 5 business ideas if the second one takes off.

Tracking goals

Once the North Star, Objectives, and Key Results are defined, you need to make sure you’re working toward them consistently. Here’s the system I designed:

  1. I keep my OKRs as a top-level page in Notion (which I use for most of my notes), so they are always in sight.
  2. I use this template to organize my work on a weekly basis. At the beginning of a week, I clone it and fill it out with current tasks. At the end of a week, I review progress by answering questions like “What got done towards quarterly/annual goals?” and “What didn’t get done that should have?
  3. I schedule setting and reviewing goals in my calendar, daily and weekly.
My calendar.
My calendar

And that’s it! This system will undoubtedly evolve, but for now, it’s an excellent starting point. Creating systems, discipline in following them, and constantly refining them are essential for success.

Let me know your thoughts in the comments below. Do you have any tips for setting personal goals?

930cookie-checkHow to set personal goals like successful companies do

2 thoughts on “How to set personal goals like successful companies do

  • Why wouldn’t you want to work 9 to 5? It seems to be healthy, standardized with other people’s schedules and helps maintain a healthy work life balance.

    • Hi,

      I meant 9-5 figuratively, as a synonym for a full-time job with a fixed schedule. I have nothing against these hours per se, but also want to experiment and see what schedule works best for me. For example, I usually feel sleepy and low on energy in the early afternoon, so I’ll try to do most of my work in the mornings and late afternoons or evenings. In my last job I worked 10am-6pm and that didn’t work very well for me, because you don’t have much time to work before lunch, then comes the afternoon dip, and then you leave at 6, which didn’t correspond with the times of day when I can be most productive.

      Absolutely agree that work-life balance is key, and that’s why I want to find the schedule that works for me the best.

      (Sorry, I wasn’t deleting your comments, I just needed to approve them before they show up)

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