Don’t narrow yourself down before you have to.
I studied architectural engineering, then pivoted to business, then technology management. At every turn, I just kept moving toward whatever was next.
Looking back, that was probably the best career decision I never fully realized I was making.
The advice I’d give my younger self is less about what to do and more about timing. I started building my business to improve estimating peer review processes when I had no dependents and no one else’s stability on the line. That mattered. I got lucky in that respect, and I wouldn’t do it again without looking hard at the full picture first.
Entrepreneurship in restoration is hard work. People see the ones who made it and assume that’s the norm. It’s not. Starting a business is draining in ways you can’t anticipate, and whether it works often comes down to life circumstances as much as it does to skill.
What I’d tell myself, though: operate with a two-to-three year outlook. Stop trying to build a 20-year plan. I’ve never done the same thing for any long stretch of time.
Stay humble, stay broad, and keep moving.
Chris Tilkov is a Director at DocuSketch and the President and Founder of 
