Corporate incentives vs. 1099 incentives

by Dale Davidson March 18, 2026

I just finished this cool business book called Simple Numbers, Straight Talk, Big Profits by Greg Crabtree.

Simple Numbers, Straight Talk, Big Profits: 4 Keys to Unlock Your Business Potential

Crabtree is an accountant with his own firm and the book is about simplifying some key financial metrics for your business so you can operate it effectively.

It is mostly not relevant to the solo 1099, however, he did mention this one thing about creating employee incentive plans to drive growth: namely the fact that they don't work!

I’ve played with incentive plans, and very few of them created the desired outcomes. Before I devise an incentive plan for an employee, I want to see a personality profile to find out if the person is motivated by money and driven by incentive plans. Very few people are motivated this way. People will tell you that getting more money will change their performance, but it’s usually more effective to use small amounts of money along the way to recognize outstanding achievement.

As an aspiring solo 1099, you may be motivated by money and generating "sales" and getting financially compensated for your effort.

But if most W2 employees aren't, this explains why it's so common for companies to give out $50 Amazon gift cards or very small spot bonuses: the employees appreciate this more than a performance based bonus plan!

Money is just one of the dimensions in which corporate incentives may differ from your personal incentives.

Companies like repeatable processes and worker bees who consistently show up; 1099s like to try new things and take Friday off to nap.

Companies want to grow sales and profitability; 1099s want to maximize their personal earnings, but not at the expense of other things they value.

Companies want employees to be dependent on them; 1099s want to be independent and self-reliant.

Part of going 1099 is facing the fact that you may not be cut out to be an employee and that this isn't a character flaw.

If you can lean into it, then you can stop feeling guilty about not being as "good" as other employees in the way companies care about.

Once you accept that, reward yourself with a $50 Target gift card ;).

Want the full playbook? Check out Going 1099.