goal setting that actually works

goal setting
that actually

“Wait, is it time for goal-setting again? I’m still recovering from 2020!”

I feel the exact same way. But heck, life goes on, and here are my 4 key steps in goal setting to get you started:


Before making plans for the year ahead, I start first with reflecting on the past year – the good, the bad, the ugly. This usually takes me awhile because I want to be brutally honest with myself, to take a step back and see the forest from the trees – I give it a couple of days, and think about it over walks at the park, while I’m brewing coffee, when I have time to draw perspective on why I made certain choices, and what that informs me about my own habits, systems and patterns. 

Since I was about nine actually, I’ve done some version of reflection and self measurement- today, I have an excel spreadsheet where I grade myself on each line item that form my goals. I certainly believe that what gets measured gets done, and this is also an interesting exercise in realizing often, how far off you can be on assumptions you made in formulating the goals a year ago – and whether a bad year or a good year, how much you’ve grown from the last time you wrote those very goals. And of course, I’ve evolved to be open and welcome line items that I did not even imagine possible because my version of myself was limited then. 



Now this is a new concept I’ve incorporated into my goal-setting, which is to create broad themes for the year or for the decade. This came about partly because I perhaps grew out of my naivety of thinking I could achieve my big goals in a single year, getting frustrated with myself in the process and am taking on the advice of some great friends this year, to “be patient with myself”. 

Depending on where you are in life, it could be RECOVERY, GROWTH, and having a big theme you can remember and tie your actions to – can I think be super helpful. 

For me my theme next year is BREAKING THROUGH – I’d love to hear what yours is in the comments below!



When I think about many of the goals I did not achieve, it all stems from the fact that they were goals I thought I should have written down because it’s what I thought was right, a checklist based on my age, by this age I need to be this, and that — but when I dug a little deeper, felt zero connection to it. In the words of Marie Kondo it did not “bring me joy”; and I know that sounds absurd, there will be things we have to do that certainly do not bring us joy, but what I’m getting at is the most important question you’ve heard me say a million times by now, which is “SO WHAT IS YOUR WHY?” Is this goal something you truly want, or is expected of you, or you expect of yourself? 


Studies have shown that often, we fail because we are not setting the right goals. No surprise, we eventually do not achieve them, and then end up tanking them all together. 


What might help you in this process is in using a methodology – SMART is the popular one, where you set goals that are Specific, Measurable, Attainable, Realistic and Time Bound. So in this framework an example would be instead of just “I want to be fitter” – it would be “I want to get to 18% body fat, and build enough stamina to complete the 4th of July Marathon”


The other methodology that I like which is useful for businesses is the OKR  – Objective Key Results.  The concept was created by Andy Grove in the 70s but popularized by John Doerr,  a popular VC who was one of the earliest investors in Google. OKR quickly became an important focus for Google, and companies such as LinkedIn, Twitter, Dropbox, Spotify, AirBnB and Uber have since followed suit.

 Doerr’s formula is the best way to explain the structure of an OKR:

For example: I think about Carrie Shaw, the CEO of Embodied Labs, one of our partner funds’ WXR’s investees – one of the Pioneers in the use of VR for Healthcare Training


Her objective of building a robust immersive training platform for companies, particularly in healthcare is centered on her personal why: her mother was diagnosed with early onset Alzheimer’s, and she struggled to explain to caregivers the exact nature of her mother’s visual impairment. Today she’s built a VR platform to help senior care workers step into the experiences of those they serve. 

If you notice the objectives are more specific than a lofty goal – they must be significant, concrete, action-oriented, inspirational.



Finally, and this is a principle I live and breathe by – that again in the words of James Clear

“You do not rise to the level of your goals. You fall to the level of your systems.”

And this is reflected in one of my favorite TEDTalks of all time- by Stephen Duneier: an ADHD child turned hedge fund success story to yardbomber – I highly recommend it!


In a nutshell, he says what ultimately stands between us and achieving our largest ambitions have far less to do with talent and capability, instead far more HOW    we approach problems and make decisions to solve them. And because of the continuous and compounding nature of those millions of decisions, a marginal improvement on our process has a large impact on our result. 


We don’t control the results but what we do are the little tiny decisions we make everyday that move the probability of us achieving this result. For Stephen, he started by calculating his commute time, 45 mins a day translated to 360 hours a year that was wasted just listening to music; he removed all music and listened to German and not too long after was able to be fluent in German, he got hooked and used this to then start auto racing, flying planes and then, yard bombing!

Running a marathon is a goal, training to run a marathon by running X miles each week is a system.


So the key here is start with the big concepts, then break them down to small manageable tasks, and make marginal improvements along the way. 


And my final piece of advice, start where you are. You probably already have some persistent habits you can use as triggers to plug in the behaviors you want to use to build towards your goals. Two of the biggest misconceptions about goal setting is that it means more work, or leads to disappointment about not being able to achieve everything you hoped. 


Really, effective goal setting usually allows you to do less by focusing your efforts on what you really do want to achieve. It also removes the disappointment of not achieving everything because unrealistic expectations are removed.


Build your momentum and celebrate little wins – and I wish you the very best of luck!