How do you feel about leaving money on the table?
Most creators are bootstrapped, meaning we’re not playing with house (aka, investor) money. Every dollar we have the opportunity to bring in seems sacred. So are you even allowed to leave money on the table as a creator?
It seems counterintuitive, but leaving money on the table leads to more income and impact.
I started thinking about this idea after an exchange with Justin Welsh on Twitter:
Learning to leave money on the table is one of the hardest mindset shifts you can make.
Trust me, I grew up on food stamps and public housing. Then, after spending 12+ years getting my doctorate to practice therapy, I got fired with zero way to get another job. So I had to bootstrap my own business (with no business background), and made $0 the first four months while I bumblefucked my way along trying to figure out how to make it work.
So the thought of saying no to money was blasphemy.
But every headache, every time I felt drained, and every moment of business I wouldn’t relive if I had the opportunity was because I refused to leave money on the table.
Here’s what I mean…
•••
Not Every Dollar is Worth the Same
When I started coaching a few years ago, I took anyone who’d give me money.
I ended up doing productivity stuff with wantrapreneurs because, honestly, it’s easy money that takes virtually no effort.
But it’s not inspiring.
Spending every session talking about the basics of time-blocking, Eisenhower Matrixes, and batching is fine, but it gets old fast. And working with people who expect you to be a surrogate for their own self-discipline is exhausting when they refuse to take accountability, or constantly talk about how they “want” to start their own business but [insert bullshit excuse here] keeps getting in their way.
There’s nothing wrong if you want to spend every day telling people to drink water, prioritize sleep, and make SMART goals, but that isn’t for me.
Every session felt like pulling teeth to get them to commit to taking action.
I started dreading looking at my calendar for the week…
That’s when I learned that not every dollar is worth the same.
Because at the end of the day, our most precious resource is time. So why would you spend it doing shit that makes you miserable? Because someone paid you a few hundred bucks?
Fuck that.
The same goes for products you create.
People who ask for discounts are 50X more likely to be a pain in your ass.
I don’t offer discounts anymore. I’ll occasionally offer a coupon or scholarship, but that’s predetermined and not based on someone emailing me saying, “Hey bro, can I get a discount? Your course looks great and can help me a lot, but I don’t want to spend money on it.” (Note: I’m not talking about people from countries with a lower purchasing power. I’m talking about entitled asshats.) More often than not, these people end up clogging up your inbox by being super high-maintenance.
I also don’t offer refunds. Not because I’m trying to swindle people (I stand behind everything I put out), but because I only want people to take my stuff who are willing to put in the effort to apply it.
People who take action don’t ask for refunds.
Every single time I’ve had someone request a refund, they said something along the lines of “Hey man, this is great, but I don’t have the time to apply it. So can I get my money back?” They’re wasting their time and mine.
So could I make more money by offering refunds, giving discounts, and taking clients who aren’t a great fit? 100%.
Is it worth the cost of increased headaches, energy drains, and dread? Not for me.
•••
Optimize for What Matters
I value my time and peace of mind more than making a few more bucks.
The reason so many of us become creators is to chase freedom and fulfillment.
But always taking money when it’s put on the table pulls us away from why we originally started creating.
Our calendars fill up with poorly-aligned obligations because there’s a dollar amount attached to them.
The more we chase money for freedom, the more it leads to our enslavement.
Freedom to me is the power to control how I spend my time. More time with loved ones, more time hanging out with inspirational people, more flexibility to take advantage of serendipity, and more time doing deep work and creating kickass content that helps creators reach their potential.
Optimizing for freedom and fulfillment requires “walkaway” power.
Being willing to leave money on the table, to say no to certain opportunities that don’t move you closer to a life aligned with your values, is the true path to freedom as a creator.
From a tactical standpoint, obviously, you need to pay the bills and take care of your family. Just be aware of when the tradeoffs stop being worth it. Also be aware of lifestyle creep. If you make $80,000 and can live off $50,000, it’s way easier to say “no” to $10k-$20k than if you make $250k but you’re hemorrhaging cash playing status games and living beyond your means.
If you’re optimizing for freedom, then optimize for freedom—not a surrogate for freedom.
•••
Be Selective to Be Effective
The real power of leaving money on the table is that, counterintuitively, it allows you to scale your income (and impact).
By saying “no” to misaligned opportunities, energy drains, and headaches, you leave tons of room open to say “yes” to truly life-changing opportunities.
By saying “no” to the wrong clients, I made room for the right ones. The more I helped them, the more they spread the word and collaborated.
By filtering out poor-fit customers, I could focus on helping perfect-fit ones get great results.
The more selective you are with:
- Who you help
- How you help them
- What you help them achieve
The more effectively you’ll:
- Build your reputation
- Create valuable content
- And yes—scale your income and impact
The alternative is diluting yourself and your content to appeal to the masses, which is how you end up appealing to no one.
•••
Wrap Up
If you want to optimize for freedom, get comfortable leaving money on the table.
The sooner you develop this power, the sooner you’ll be able to filter out distractions, headaches, and energy drains, and double down on scaling your income and impact as a creator.
I’m not a dentist, so I’m not in the business of pulling teeth. If working with someone or taking advantage of an opportunity will feel like pulling teeth, I’d rather leave the money on the table.
Now, one question I ask myself before signing a client, doing a workshop, or collaborating on a project:
Would I work with this person for free because of how energizing and inspiring they’d be to work with?
If the answer’s no, I pass.
Have I left tens of thousands of dollars on the table?
At least.
But have I loved every second of every person I’ve worked with since I started asking this question?
100%.
•••
Question for the Week
What steps do you need to take to have the power to leave money on the table?
•••
If you’re curious, here are a few courses to help you level up your life and business:
- World-Class Coaching : Learn the systems the best coaches in the world leverage to charge $500+ an hour.
- Core Value Toolkit : Ever wanted more clarity on which direction to take your life? I call that your Core Value, the single most-important value a life well-lived must be built around. This toolkit is the first step to clarifying yours.
