Ah, the benefits of hindsight. If we "knew then what we know now," our financial portfolios would appear much different. We might not have wasted so much time on that startup idea. We certainly would not have crashed and burned at the presentation trying to get seed funding.

The list goes on.

At the same time, any exercise in Monday Morning Quarterbacking can also trigger a surge of reflected accomplishment. Every business owner has experienced struggle and failure, but the successful ones understand that's useful time spent, and can be counted in the currency of experience.

With that in mind, I polled dozens of CEOs and funders and asked them the question:

What one nugget of information would you pass to your younger self?
1. Take more risks. It exposes you to new experiences that build your confidence and resilience. The biggest turning point in my career happened when I stepped outside my comfort zone; it was a high-risk move into a role that put me on a new trajectory. The experience was exhilarating. -- Gerald Hassell, chairman and CEO of BNY Mellon

2. Get enough sleep, eat healthy and exercise. There is no virtue in deprivation. You as an entrepreneur perform much better for your business as a result and the hours and money you save by skimping on these have a negative return, especially in the long run, for both you and your investors. -- Siggi Hilmarsson, CEO and Founder of Siggi's Dairy

3. It's acceptable--and advantageous--to show emotion and to demonstrate appreciation, to "pull down the curtain" and let people know you experience the same challenges and reactions to situations that they do. Remarkable things can happen when people know they are trusted, valued, and recognized for their efforts. -- Bill Johnson, CEO, Citi Retail Services

4. Whether it's people, products, or ideas, push the winners harder, and get rid of the losers faster. It's very important to identify high performers early on, and continue to grow them. It's also just as important to understand where underperformance is occurring, and to eliminate those points of weakness. -- Hari Ravichandran, founder and CEO of Endurance International Group

5. If it's hard, make it easy. Changing your mindset can dramatically influence the quality of each moment. -- Lynn Jurich, CEO, Sunrun

6. Surf a little less, go to class a little more. - Mike Cagney, CEO & co-founder, SoFi

7. Avoid blindly listening to "the experts," they're wrong--a lot. Trust your intuition and place real value in your personal experiences. -- Crowdtap CEO Sean Foster

8. Don't confuse love with passion. Love will beautify the business you're in. Passion will grow it. -- Piers Fawkes, founder & CEO, PSFK

9. I would have told my younger self to "Buy domain names." Almost all of us missed a gold rush. A tiny percentage of people bought a bit of digital real estate for a few hundred dollars and sold it later for millions. -- Andy Crestodina, Principal, Orbit Media

10. Think Big. When thinking big becomes a part of your management DNA, you'll be surprised at what you can achieve. -- Stephen Baker, CEO of Attivio

11. I would tell my younger self about the miracle of compound interest, or what Albert Einstein once called the 8th wonder of the world. When you're young, it's hard to think about personal finance in the future tense but invest, save and pay close attention to the state of national and international markets; you'll reap the rewards later. -- Gino Blefari, CEO HSF Affiliates

12. Have the courage to make decisions faster. Above all, make tough decisions faster. It's your responsibility as a leader to put the company first and quickly make decisions that are in the best interest of the organization. -- Andreas Bodczek, Chief Executive Officer, co-founder, Fyber & RNTS Media

13. If you have an idea that you know-in your bones--is a winner, don't let it go. It may not work today, it may not work tomorrow--but a good idea will always find a way to surface and succeed if you keep it alive. - Tapad CEO and Founder, Are Traasdahl

14. Keep doing what you're doing. Focus on being the best, keep reaching for the moon and you'll come down with a hand full of stars. -- Larry D. Young, President and CEO of Dr Pepper Snapple Group

15. Under-promise and over deliver to your boss. Make them better and you will be indispensable. -- Sloan Gaon, CEO of PulsePoint

16. Don't buy stuff with the little money you have, spend it on experiences instead. There is so much stuff that one can only do at certain stages of their lives, make sure you take full advantage of this. -- Dominik S. Richter, Global CEO & Founder, HelloFresh

17. Listen to people and be receptive to constructive criticism, but do not be overly influenced by everyone, especially the naysayers. It's easy to fall into the trap of being malleable to every single feedback thrown your way. Be confident and trust that you know the potential of your business model best. -- Aydin Acar, CEO and Co-Founder of Influenster

18. Have patience. Have more patience. But now I have more patience because I don't have as much "joost" -- Alan Miller, CEO of Universal Health Services

19. Take up space--a lot of it. Young girls and women are taught to shrink themselves in and outside the workplace. I'd tell my younger self to speak up--loudly. To own the space she occupies with big ideas, big gestures, big enthusiasm and big whatever else it takes for her to communicate with conviction. I'd tell her to never shy away from being fully present and accounted for in a room. -- Brandee McHale, President of the Citi Foundation

Published on: Oct 20, 2015