I've written at length about seeing things through and how cultivating the habit of grit, determination and persistence was one of the biggest breakthroughs in my ability to deliver real world results.
7 years later, I still stand by this assertion that developing staying power so that you can outlast your competition is one of the most consistent ways of achieving success.
What I've come to realize, though, is that seeing things through is not just about brute forcing your way through the dip. It's equally about being intentional and deliberate about what you choose to take on before you've even started.
To Choose a Battle
Should you really commit or not?
The absolute worst-case scenario? Being a year deep into a project before it hits you: "I never should’ve started this".
You’ve poured in time, energy, maybe even money only to realize that if you’d taken a step back and looked at the bigger picture from the start, you’d have made a very different call. That kind of regret stings.
I’ll admit it - I’ve definitely been guilty of this. My default mode is to get overly excited and jump straight into action. Punch first, questions later. Build an app Let’s go. Start a company? Why not. Write a book, launch a video course, train for a marathon, take up ice hockey? Sure, sounds amazing - in that first flash of inspiration.
Every new idea feels like the one when it first hits. It’s easy to get swept up in that initial momentum and skip the whole “pause and think it through” part.
To avoid falling into that trap, I’ve put a kind of safety net in place - a personal framework made up of key questions and writing prompts. It acts like a checkpoint, forcing me to pause before I dive headfirst into a project that might not actually make sense.
This simple process helps me ask the right questions at the right time - before any code is written, any money is spent, or any energy is burned. The result is that I’m far more intentional and strategic about what I commit to. I finish more of what I start, and I avoid the painful realization halfway through that I’m climbing the wrong mountain.
I’ll share that list of questions with you at the end of the post - but first, I want to walk you through some of the books, ideas, and teachings that helped shape it.
The Dip by Seth Godin - Is the Battle Worth it?
One of my favorite books on this topic is The Dip by Seth Godin.
In it, Seth describes “the dip” as that inevitable stretch of difficulty that shows up after the initial excitement of starting something, but before you’ve reached any real success. It’s the slog in the middle - the grind - where things aren’t fun anymore, results are slow (or nonexistent), and you start to wonder what you got yourself into.
If you’re building a startup, it’s that moment a few weeks or months in when the adrenaline fades and the real work begins with little feedback, no traction, and plenty of uncertainty.
But the dip isn’t exclusive to business. It shows up in any meaningful pursuit. Learning to salsa dance? There’s a dip. Fumbling through the basic steps, missing the rhythm, stepping on feet (sorry!) all before you gain enough skill and confidence to actually enjoy dancing freely at a club.
Godin’s key insight is this: not all dips are worth pushing through. The trick is to be strategic and intentional about which dips you choose to take on and to quit the ones that don’t matter, so you have the energy to endure the ones that do.
Here are some of the questions he says you should ask yourself:-
- Is this dip going to lead anywhere meaningful or nowhere?
- Can you realistically push through this?
- Do you care enough to suffer for this?
- Is there a significant upside on the other side?
- Is this aligned with your values, strengths, and goals?
The Dip - Seth Godin
4,000 Weeks - Every Yes Comes with an Invisible No
4,000 weeks is how long, on average, you have on this planet.
Oliver Burkeman, in his brilliant book 4,000 Weeks, takes a more philosophical and time-focused approach to the question of what we should commit to. His perspective is grounded in the stark reality that time is finite. Every “yes” comes with an invisible “no” to something else.
The opportunity cost of doing anything, whether it’s launching a business, taking on a side project, or even just saying yes to another meeting, is that you’re not doing something else with that same slice of time.
It’s a humbling thought, and one that forces a deeper kind of intentionality: If you only get around four thousand weeks in a lifetime, what’s really worth spending them on?
You can’t do it all. So what is actually worth doing deeply?
Here's the advice he offers about committing to a project:-
- You'll never have time to do everything, so choose wisely
- Saying no is not optional - it's the only way to go deep (you have to say no to most stuff to properly say yes to what matters)
- The more you try to do, the more you end up skimming the surface of everything and mastering nothing.
- You don't need to do everything - you just need to do what’s deeply aligned and worth the trade-off.
4,000 Weeks - Oliver Burkeman
The fact that we each get, on average, just 4,000 weeks to live is a sobering thought. And if you’re anything like me, you’ve probably already burned through a fair chunk of them.
The takeaway? We need to get far more comfortable with saying “no.”
Not out of fear or laziness, but out of respect for what truly matters. Time is a limited resource, and the more we scatter it across things that don’t align with our values or long-term goals, the less we have for the stuff that actually counts.
Tim Ferriss - "Can I Succeed even if I Fail?"
Tim Ferriss, bestselling author, entrepreneur, and podcast host best known for The 4-Hour Workweek and his insights on productivity, lifestyle design, and self-experimentation had some interesting insight to share on what criteria to decide whether to embark on a project.
As you’d expect, Tim Ferriss has a well-thought-out framework for deciding what to commit to - and, just as importantly, what to avoid. Here are some questions and additional criteria that goes into his decision making process:-
- Will this project help me to develop or deepen skills?
- Tim biases towards projects that offer opportunities for skill development. For example, he started his podcast in part to improve his ability to ask questions, reduce verbal ticks, and refine his interviewing skills, which would transfer to his future non-fiction books
- Will this project develop or deepen relationships?
- Similar to skill development, Tim considers which projects will help him develop or deepen relationships the most, even if they fail by external metrics. His podcast also served as a pretext to deepen relationships with close friends and reach out to people he wanted to get to know
- Can I succeed even if I fail?
- He asks this question to evaluate potential projects. If a project helps develop transferable skills and relationships, then even if it fails by external metrics, he considers it a form of success. This is described as an "inverse Pyrrhic victory" or a "Successful Failure"
Along with these questions, Tim also has other criteria that he uses to increase his chances of seeing things through:-
- Focus on short-term experiments: He tends to focus on short-term projects, typically three months, which often involve two to four week experiments. He views these projects and experiments as feedback mechanisms rather than binary success or failure outcomes
- Preserving optionality: He prefers not to commit to long-term, fixed plans, such as multi-book deals, to preserve his optionality and be able to take advantage of attractive, unforeseen opportunities that may arise
- Considering long-term accumulation: He evaluates the potential of a project to accumulate value over a longer period, such as 3 to 5 years, focusing on the transferable skills and relationships gained
- Avoiding purely financial motivations: While acknowledging the importance of financial stability, he suggests that purely chasing money as a primary driver can be problematic and that focusing on intrinsic value and personal aliveness is more sustainable
Tim Ferriss
11 Of the Most Important Questions to Ask Yourself Before You Commit
Each of these thought leaders tackle the challenge of commitment from a different and valuable perspective:
- Seth Godin approaches it as a practical risk-to-reward analysis. Is the struggle worth the potential payoff?
- Oliver Burkeman zooms out to focus on time and opportunity cost. What are you giving up by saying yes?
- Tim Ferriss frames it around resilience - how to structure your commitments so that even failure becomes a win especially when it comes to deepening skills or relationships.
Drawing on insights from all three, I’ve developed my own list of 11 questions - a personal filter I return to whenever I’m deciding whether something truly deserves my time and energy.
11 Questions to ask Yourself before Committing to Something
- Who am I really doing this for - me, or someone else?
Is this driven by internal motivation, or am I trying to impress, please, or prove something to someone else (family, friends, associates)? - Does this align with the person I want to become?
Is it in line with my values, identity, and long-term vision for my life? - Do I truly have the time, energy, and resources to follow through?
Am I being honest with myself about the commitment this will require? Can I get through the dip? Have I done the necessary research to make a good call on this? - What does success actually look like — and will it be worth it?
If everything goes according to plan, will the result be meaningful or fulfilling? Will it all be worth it? - If it “fails,” can I still turn it into a win?
Will this deepen my skills, grow my relationships, or leave me better off in some way regardless of the outcome? - How can I make this a lopsided bet?
Is there anything I can do to limit the downside while retaining the upside? What stop losses can I put in place? - What’s the real motivation behind this?
Am I chasing money, recognition, or status - or am I genuinely excited and curious about the work itself? Be honest. - What am I giving up by saying yes to this?
Is there something else more aligned with my goals that I should be doing instead? - How many of my ~4,000 weeks am I willing to invest before reassessing?
What’s my checkpoint for stepping back and evaluating whether to continue? - Am I trying to force something that isn’t flowing naturally?
Is this coming together with clarity and energy, or does it feel like pushing a boulder uphill? Is this aligned with my strengths? Am I good at this? - Would I still choose to do this if no one ever saw the result?
If the outcome was never shared, praised, or monetized - would the process still feel worth it? Is it about the journey or just the result?
The real magic comes by treating these questions as journaling prompts. There's something about writing things down that brings clarity that thought alone cannot.
Deciding What to Commit to is Value Investing for Time
A value investor looks for assets the market has overlooked - buying them for less than they’re truly worth, and waiting patiently for the world to catch on. Warren Buffett, the GOAT of value investing, built an empire on this simple but powerful principle.
Now flip that idea around: being intentional about what you commit to is value investing for your time.
You wouldn’t throw your hard-earned money into random stocks just because they looked shiny for a second, so why treat your time any differently?
And here’s the kicker: time is even more valuable than money.
You can earn more dollars. You don’t get more hours. That’s exactly why it’s worth slowing down, asking the right questions, and choosing your commitments with care.