How to get started on your goals with small wins

Updated to Productivity on March 26, 2024.

I’ve noticed a problem I think we all share.

It’s an insidious disease that seems to have infected pretty well everyone I meet. And there’s no vaccine, surgery, or Ayahuasca ceremony to cure it.

What’s the problem?

It’s not getting started.

People talk a big talk, like “I need to burn off those Christmas pounds”, but don’t get started. Just last week, people told me they wanted to: “improve team morale”, “figure out where all my money goes!”, “find time to take better care of myself” and more.

January, when I’m writing this, is the zenith of promise-making drama. This is when we rush to make resolutions, reexamine our habits, and spend evenings watching YouTube gurus talk about intermittent fasting, cold plunges, and weight training. 

The problem is none of that works if you don’t know how to get started. It’s like declaring you are going vegan but not having any idea what to shop for or what recipes to trust.

There is research supporting a sort of “active procrastination” – self-aware individuals who make strategic choices to postpone certain work in favour of higher priorities. But, that’s not what I’m talking about.

I’m talking about good intentions that get all dressed up but never go to the dance. And if you don’t go to the dance you aren’t closing the gap.

Let me explain.

Enter the gap

We all have gaps between where we are in life, work, relationships, health, etc., and where we want to be. Those gaps are not bad things you want to avoid—they are actually the source of healthy living. Striving to close gaps in life is as essential as drinking water because it creates what is known as eustress – the good stress that motivates us and makes life meaningful.

The challenge comes when we avoid the gap – procrastinating and making excuses for not getting started. It sounds like this: “There’s never enough time to…”, “As soon as I….”, and “I’m always doing that!”

Put me in front of any audience and 99% of them have a gap they haven’t tackled. That’s the wrong kind of stress. Getting Things Done author, David Allen says most stress is created from unfinished tasks—we know what we need to do, but are paralyzed by inaction. 

Often, we don’t get started because we haven’t built the muscle memory to know how.

The trick is to jump-start your goals.


When I was a kid my first car was a Datsun 110. It was an ugly box of a car, but to me, it was wonderful. That car took me to work, university, parties, and my girlfriend’s house. 

Given the condition of the car and my nonexistent repair budget, I would often have to jump-start the beast. I got so good that by pushing against the open driver’s side door I could get a rolling start, slip in, pop the clutch, and be on my way. 

Jump-starting your goals might not always go smoothly – sometimes, like my car, it might stall altogether – but at least (and here’s the punch line) you are moving forward.

Here are some examples of how I jump-started some goals in my life and created small wins.

Small wins

Small wins are short, easy tasks that take you one step closer to your goal. A good jump-start on your goals should lead to a small win. I wrote about small wins and how to create them in this post

Here are five ways I’ve jump-started goals and created small wins:

  1. Plan your week. This is possibly my most recommended small win. Start by taking 10 minutes to review the past week, outstanding work, and your goals for this week. As serial author, Cal Newport wrote “Clarity about what matters can provide clarity about what doesn’t.” 
  2. Block the time. Once you have planned your week keep the flywheel going by turning work into blocked time on your calendar. I first learned this strategy from Cal Newport and have since incorporated it into every program I teach on productivity. 
  3. Clean your desk. If you want to clean up the “clutter” in your life, start with the workspace you spend hours at every day. Just because Einstein, Edison, and Jobs had messy desks doesn’t mean you should. When I take five minutes to clean my desk it’s a reminder that I can control my work experience. 
  4. Create an agenda. Stalled out knowing there is a meeting you need to create, but don’t know where to start? Create an agenda. I find that a few minutes of mapping out what needs to be discussed helps clarify the purpose and urgency of the meeting. Plus, when you launch the meeting you now have the agenda ready to circulate.
  5. Learn from others. We’ve all gone to YouTube to solve some technical problem or find a fix for something broken at home. What about jumpstarting your next goal? As Emerson said, everyone is better than us at something—even if it’s a little thing. I’ve watched TED talks that inspired a new workshop and listened to podcasts that helped me negotiate the sale of my business. 

Your gaps

What are your gaps this year?

Some readers have written me about their fitness goals, others are working on carving out time for hobbies put off during their careers, and others are growing their businesses.

Life is all about closing the gaps. Every time you jump-start progress you move closer to your goal, you also build muscle memory for how to do it next time. 

Just like learning how to do intermittent fasting, take cold plunges, or lift weights, finding the jumpstart for every goal gets easier with practice.