Chopping Wood

“Give me six hours to chop down a tree and I will spend the first four sharpening the ax.”

-Abraham Lincoln

There’s a term I like to use when in the middle of something challenging and of significance… “just keep chopping wood”. Today I find myself “chopping” away at one of the most challenging and rewarding experiences of my professional life while co-founding an emerging Venture Capital firm. There’s a lot of chopping and it’s one hell of a tree trunk!

But chopping wood isn’t just about taking hacks at a stump. It’s about finding the right tree, calculating where you’d like the tree to fall, knowing where to strike and then staying out of the way once it starts to fall. The following short read captures my thoughts about how we can all chop more efficiently at anything we see of value in our lives. With a little concentration and a lot of grit any one of us can knock down the biggest trees. So strap up your boots and grab your axe, we’re going into the forest… TIMBER!!

Disclosure: No trees were harmed during the making of this post. I’m using this as a metaphor and don’t condone deforestation. I’m actually a huge fan of nature and the principles of leaving no trace.


Have you ever spent countless hours working on something that turned out to collect (digital) dust? I know I have. Afterwards I always feel accomplished but find that nothing of value came from the work.

When entering the forest it’s important to spend some time looking for the right tree to chop. If you just swing away you’ll end up chopping down the wrong trees, or even worse, take a bunch of hacks at trees that never end of falling. It might be a good workout, but you’ll never leave with a payload of any value.

Now not all trees have the same trunks sizes (value) and that’s ok. Sometimes you need a Sequoia to build a home (i.e. career change, major investment) and sometimes you need a small Douglas Fir for a family holiday (i.e. new hobby, vacation). Just make sure you know what tree you need before you begin chopping.

So take some time to not just scan the forest, but to think about what kind of tree you’re looking for. There are a lot of great books on finding the right opportunities in your life to focus on, and Essentialism: The Disciplined Pursuit of Less is one of my favorites. The author, Greg McKeown, makes the argument that the pursuit of less doesn’t mean you’re less busy, it means that you have time on your hands to better evaluate the opportunities that you do pursue. You can’t wander the forest in search of the ideal tree if you’re always chopping away at the next tree you pass.

Takeaway #1: Scan the forest to make sure you’re looking for the right trees before you ever take your first swing. This will help make sure your time and energy are spent on the right outcomes.


There it is! After scanning the forest we’ve found that beautiful tree we want to focus on. It has a pretty big trunk, but with a lot of effort and focus we’ll bring this thing down.

Now before we pull out our axe, it’s important to know where we want this tree to fall. What is the ideal outcome here? What is the least desired outcome? Answering these questions ahead of time won’t just help us make sure we’re concentrating our swings of the axe but can also help revalidate that we’re focusing on the right tree in the first place.

You can think of this as the “measure twice, cut once” principle that’s used in carpentry. It’ll be much easier for us to find another tree if we’ve yet to take any swings and exert any energy. This will also help us avoid completing projects that we already know won’t bear any valuable results, something referred to as the sunk cost fallacy.

Takeaway #2: Once you find your tree make sure you look around to see where you want the tree to land. If you found the right tree but the wrong landing space, then it’s ok to keep searching the forest. There are a lot of trees out there.


Alright here we go! We’ve found our tree and know where we’d like for it to fall. Now it’s time to take out our sharpened axe and get to swinging.

Swings of the axe are a lot like tackling the little roadblocks we find along the way. Chances are that the bigger the opportunity, the more of these “speed bumps” we come across. That’s ok, because we’re seasoned lumberjacks and know how to approach these challenges as they come up. We’ll just want to remember to:

  • Focus on where to strike because a bunch of random swings won’t drop a tree. You’ll want to first know where you want the tree to fall and focus on making sure each swing gets you one step closer to that desired outcome.
  • Conserve your energy tailored to the size of the trunk you’re chopping. You don’t want to use too much effort (stress, time) on those first few swings. Some trees take dozens or even hundreds of swings.
  • It’s ok to catch your breath in between swings, we may be out here for awhile. Just like it’s important to conserve your energy, it’s also ok to step back, catch your breath and to make sure you’re making the right progress.

Takeaway #3: Swings of the axe, like roadblocks, are inevitable on anything worth pursuing. Make sure you take time to focus on where you’re striking, stay persistent and keep chopping wood.


With enough chopping and effort you’ll eventually hear that deep cracking sound. Oh yea… that tree is finally starting to come down!

You’ve spent some time evaluating where you want the tree to fall and have been chopping strategically, but sometimes these kinds of trees can be unpredictable. Especially the larger trees that land with more force. Once momentum build it’s best to stay vigilant, but get out of the way when that tree starts to move.

An example I’ve seen over and over is the poor practice of over selling. A deal’s been agreed upon with terms locked in, and an individual continues to pursue new avenues or raise new ideas. Once you get to that “yes” then it’s ok to step back and stop chopping wood.

Once the tree lands and settles you can strategize on where to move it next (i.e. next steps, kick-offs, relationship handoffs). While the trees in mid-air (i.e. final negotiations, signatures) it’s ok to sit back and watch nature do its thing. Sometimes the tree won’t land where you originally intended, but there’s little you can do to change that mid-fall.

Of course, there are exceptions here especially for larger trees. Hopefully you’ve spent time looking for the right tree (i.e. client or partner), calculated where you want it to fall (i.e. desired outcome) and have been strategically chopping away (i.e. negotiating commercial terms).

Takeaway #4: Once you hear the cracking of the wood stay out of the way. Best case the tree lands where you intended, and worse case you can move it once it’s settled. Nothing is worse, however, than having that tree land on your head.

Congratulations, you just cut down one magnificent looking tree! As any seasoned lumberjack knows, you are only as good as your last haul. So enjoy the celebration but don’t spend too much time outside of the forest… there’s more trees to chop.

Just make sure to remember to scan the forest before you start chopping away. You’ll find that you won’t only knock down more trees, but you’ll get better and better at doing so over time.

If you’ve made it this far that means that you (hopefully) got something from this post. For that I am grateful. This has been a tiny little tree but one I’ve enjoyed chopping. Now time to get back to that big Sequoia I’ve been working on… CHOP CHOP CHOP!!




“The more I learn, the more I realize how much I don’t know” — Albert Einstein

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Marcos Fernandez

Marcos Fernandez

“The more I learn, the more I realize how much I don’t know” — Albert Einstein

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