Growing up my parents told me that if I worked hard then I would be able to play hard. Something about that saying always confused me. I assumed it meant that if I worked hard in school then I would be allowed more time to play outside with my friends. And throughout high school and college, this phrase kept spinning through my mind.

I also watched both my parents work long days and sacrifice many of life’s joys in order to make time for work and one day I suggested that they should “work hard and play harder.” That didn’t seem to go over so well!

Later on, I saw the “work hard, play hard” motto when I entered my first job working on the trading desk at RBC Capital Markets. I witnessed colleagues around me putting in long and stressful hours every day from 5am to 6pm and then rinse and repeat daily year after year. I also saw fortunes made overnight and lost in the blink of an eye and I started asking myself if this working harder mentality really made people happier or even more successful.

A decade into working in institutional finance I reconnected with a colleague who left finance and went into the startup world. They said you should try to “work smarter, not harder.”

Such a simple turn of phrase struck me. This new mindset was intriguing and I wondered why no one ever mentioned it to me when I was a child.

What did “work smarter” even mean? I initially defined it as using logical skills to minimize repetitive tasks and extra steps. I then questioned why someone would say “work smarter NOT harder.” Why was working harder viewed in such negative terms? I thought that this mindset could be especially damaging to those just starting out on their career paths. Telling a fresh college graduate to not work hard, to take the path with the least resistance could set unrealistic expectations.

Working Hard And Smart

I’ve come to realize that my problem wasn’t hard work or smart work, it was the “not” in-between that confused me. Blindly working hard rarely allows you to get ahead, and working only smartly rarely develops that grit and determination mindset in the field to survive those failures and setbacks. So how can we access this third way of smartly working hard?

There are thousands of founders out there whose stories of hard work and determination often get overlooked and forgotten as most people only see the end result. Most people always focus on the billion-dollar outcome or the most recent successes without understanding the hard work that went into getting there. How many founders have had several bankruptcies and personal tragedies where they mortgaged their homes and pivoted their companies several times while sleeping on friends' couches before finding success the fourth or fifth time around?

If you ask most people what they believe the definition of hard work is, they would probably say it’s someone who burns the midnight oil or works on weekends and rarely takes a vacation. I believe this view of hard work gives younger generations a misguided view of hard work and could cause them to avoid those careers in exchange for more luxurious career paths.

I believe the true definition of a hard worker is someone who develops the skills of persistence, tenacity and hustle while accomplishing any task in order to be able to depend on those traits when they finally happen upon success one day in the distant future. I find those individuals that have developed those traits and have endured setbacks and hardships throughout their career, are much better at understanding their own successes and appreciate them more when the time comes. I fundamentally believe that those individuals who achieve overnight success without developing that hard work muscle often don’t hold onto their success for long or understand how to repeat prior successes given it was so effortless the first time around.

Here are some tips for working smarter:

• Focus on two or three priorities and stop attending meetings or devoting time to things that don’t help you accomplish your key goals.
• Say ‘NO’ more often. Don’t attend meetings you don’t need to be at if you could be working on things that help you drive your priorities.
• Don’t try to be all things to everything and everyone. Delegate projects and tasks to others to free up your time and mental bandwidth.
• Use more productivity/time-saving tools (Calendly, Superhuman, Zapier, IFTTT, Trello, Notion, Slack, Airtable)
• Block your calendar for personal task
• Keep your to-do list short, don’t put everything on your shoulders to get done or else nothing will ever get completed
• Establish a morning routine. Taking care of your body and mind is the most important and smartest thing you can do. Sleep, exercise, and relaxation will make you more successful.

Here are some tips for working harder:

• Don’t let NO’s stop you. When failure happens, some people get paranoid and fear that this may become a trend. Failure should be expected rather than feared. Learning lessons from failures and analyzing what went wrong is the best way forward.
• Keep measuring your successes. If you find success, analyze what you did right and what led to your success and try to replicate it.
• Don’t look at someone else’s plate. Focus on yourself and what you have and can achieve.
• Measure your results, not your time. Just because you have invested hours into a project or a client doesn’t mean you should lower your expectations.
• Make new contacts and always find time for networking outside of your existing contacts
• Learn as much as you can when around smarter people. Reach out to important people and connections and ask for advice.
• Most importantly, don’t always look for the shortcuts, sometimes the longer and more difficult path results in the best and most rewarding outcome

As a VC, how do we assess if a founder works smarter and harder?

• Founders who are well prepared for meetings with an agenda and expected outcomes
• Founders who use productivity tools to measure their team's performance and their own
• Founders who do their own research and don’t accept other people’s advice as gospel
• Founders who will put in the work to do things that can scale (short term pain for long term gain)
• Founders who put their team and company first
• Founders who manage their time effectively and delegate tasks to those who are far more capable then they are
• Founders who know their own limits and recognize when they are not the smartest in the room

Hopefully, these tips and tricks will help guide you to becoming a smarter and harder worker. Also, the next time you ask someone if they are a hard worker or a smart worker, double-check your definition of hard work and see if it means what you think it means?

Lastly, the most important thing to remember is that you should know when you are ready to switch off that computer and not fill up the time with even more work and useless tasks. Once you’re on track to working smarter and harder, you will find more fulfillment in your personal and professional successes.

Enjoy working smarter AND harder!