In my early years of entrepreneurship, I was intensely focused on setting big, hairy, audacious goals and shooting for the moon. My approach involved dreaming big, working hard, and rallying the team around the exciting opportunities ahead. Over time, I’ve become more tempered, setting a big vision but adopting a more measured approach to the incremental steps needed to achieve it.
It’s straightforward to declare, “We’re going to sign 1,000 customers in three years.” However, it’s a different proposition to articulate a vision of winning the market and becoming the de facto standard. For example, planning to sign 50 customers in the first year, 100 in the next, then 200, 500, and finally 1,000 allows you to maintain a big vision—like a computer in every home or organizing the world’s information—while adopting a more measured approach to achieving it.
Over the last 24 months, the software industry has been in a recession. This period has necessitated numerous reforecasts in our businesses. A reforecast involves reassessing your plan partway through the year upon realizing the original goals are unattainable—not just challenging, but so far from achievable that a new plan for the remainder of the year is required, aiming for better alignment, efforts, and outcomes.
During this software recession, the need to conduct several reforecasts each year has underscored to me that setting unrealistic goals can actually harm startup morale. Goals should be challenging yet achievable. With good faith, effort, and smart, diligent work, they should be within reach. However, if goals are unrealistic and the team’s efforts fall significantly short, this can have detrimental effects.
As an entrepreneur, it’s crucial to find that balance for your organization—setting ambitious goals without making them so lofty that they become unrealistic and harm morale. It’s a delicate balance with no straightforward solution. Entrepreneurs would do well to find their own approach to this and be intentional about how they lead their organizations in respect to goal setting.
David Cummings on Startups 
Love this post David.
I’ve come to the same realization lately in my career.
As Bill Gates said, we over-estimate what’s achievable within a year and under estimate what’s possible in a decade.
But to play the decade long game, we have to maintain the morale alive thru the rough patches.
A great example is the story of AWS which is a terrific example of compounding but also humble starts https://x.com/thisiskp_/status/1750955166377926755?s=46&t=3M0KdWHI2R4FjKbL-WWA5A
Ps: It was great running into you at lunch last week. Very proud by what you’re able to achieve in your career and how much good you’ve done for our city – and inspired by your massive ambition which helps me level up in my own way!
Best, KP
KARTHIK PUVVADA (KP) https://twitter.com/thisiskp_
Hey David,
I’m curious how you would marry this concept with the concept you expound on in your blog post, “Think About the Growth Curve from Right to Left.” Both seem critical. Gotta dream to achieve greatly, but also don’t want to harm morale with unrealistic goals. How do you think about connecting these?
Also, huge shout out to all the effort put into this blog. I just stumbled upon it this week and have devoured 40+ posts and taken several notes. Thank you!
Best,
Erik Larsen