12 Things I Wish I Knew When I First Started Working

February 28, 2017

by Ravi Raman

One third of your life if spent working, amounting to about 90,000 hours. I’m beyond the half-way point now, about 45,000 hours into it.

My working life began in college, where I sold my super detailed class notes to other students (legally!). The pocket money fueled my growing cycling and triathlon habit.

Then, I found real employment as an intern in the accounting department of a struggling airline. While far from awesome, it did help me realize what I didn’t want out of work (repetitive tasks) and what I did want out of it (dynamism and a more exhubertent work environment).

After that, I landed a summer gig in asset management at a now defunct investment bank. This taught me that even the most sexy and prestigious jobs can be monotonous, boring and lacking of purpose.

Finally, I spent about 14 years at Microsoft Corporation (great place to work!). I learned a lot here, particularly about how to work with others to solve problems that seem impossible at first glance.

Now I’m an entrepreneur – having made the leap to being an Executive Career Coach. The learning continues!

Over the years, I’ve learned a lot about how work can impact life and vice versa. I’ve seen what helps people get ahead and what holds people back. I’ve learned what to do. I’ve learned what not to do!

While I hold zero regrets about the mistakes and missed opportunities of my past, if I could relive life there are plenty of things I would do differently. This paradox is something I’ve grown to accept, being able to see my past as perfect, and yet admit that if I could have a “do over,” I would certainty make a few changes.

In this spirit, here are 12 things I wish I knew when I first started working:

1) Be an outstanding communicator

Lots of people are smart.

If you made it to a career at a reputable company (or have the guts to start your own), chances are you are smart too. Being smart isn’t enough.

Your ability to communicate is a massive factor in your career success. The top people in a company are rarely the smartest. They are the smartest that also know how to present themselves well.

Learn how to communicate — through writing and presenting. Find out how to introduce complex ideas and arguments. Don’t fear negative feedback. Keep refining the skill.

Not sure where to start? Join Toastmasters, hire a coach, or even better, volunteer a toast at the next wedding you attend (I did this twice in recent years!). Pitch an idea for a local Ignite or TED-style gathering (I’ve also done this). There are countless opportunities to practice and improve your communication skill.

2) Don’t let perfect get in the way of great

Don’t let the perfect be the enemy of the good

Shakespeare, Voltaire and Confucius

Author and technology management consultant Geoffrey Moore has a phrase, “Go ugly early.” It’s directed at innovators trying to make products that can jump across the chasm that separates winners from losers.

In the technology industry, an MVP or Minimum Viable Product is a often an initial stop in the quest for product/market/fit. An MVP is a way to get a product out the door, gather feedback, and perfect it over time.

Whatever you are doing, strive to be great, but the first step is getting out there and making something happen.

Learn from the experience of shipping your product, service or art.

3) Get strong

You can be anything you want…but you must be strong first.

Pavel Tsatsouline

There is a reason why even the busiest CEOs make time for rigorous exercise.

Get in the weight room. Do some deadlifts. Swing a kettlebell and build some strength (kettlebells have a “What the Hell?” effect).

Not into weights?

Wondering why I would include this in a list of work-related advice?

All the hours sitting at work will take its toll on your body. Exercise is the antidote. The added muscle will be a major confidence booster. The hormonal response of hard workouts will also help you cope with work-related stress. Stress can derail the brightest of careers if not kept in check.

Lifting heavy weights will force you to learn proper form and posture (or you will get injured). Strength will help you stave off repetitive stress injury. Strength workouts are also proven to provide significant cardiovascular benefits associated with endurance sports.

Hire a trainer to teach you the basics of Olympic and Power Lifting technique. Commit to getting strong and witness the positive spillover effect at work.

4) Learn how to set boundaries

Daring to set boundaries is about having the courage to love ourselves, even when we risk disappointing others.

Brene Brown

There is an infinite amount of work to do.

Learn to stop tasks and projects even if they aren’t complete so you can leave work on time. Don’t check your email after hours or on weekends. Avoid multitasking (it’s a myth anyway). Work hard when you need to and cultivate the discernment to know when to shut work off.

Build this habit early in your career, and it can help you get more done in less time, save your relationships and keep you sane.

5) Become an early riser

Ben Franklin wasn’t joking when he said:

“Early to bed, early to rise, makes a man healthy, wealthy and wise.”

I don’t care if you think you are a night owl. You can learn any habit, including the habit of being an early riser. I have yet to meet a productive and successful person who does not have an early start to her day.

Strive to join the 5 AM Club, or at least the 6 or 7 AM Club! You will be more productive and able to work in peace without the demands of the world creeping in.

Pro Tip: If you want to wake up earlier, go to bed earlier!

6) Improve your financial literacy

There is a game played around you, and it’s a money game.

You need to master the game of money early in your career. It can mean the difference between retiring with financial freedom and just scraping by in your golden years.

The reason I was able to quit my job and travel the world for 18 months was due to a long history of saving and investing since I was a teenager. I learned the basics of investing by watching my dad. I learned the merits of frugality from my entire extended family (a family of immigrants). These habits created a financial cushion as both my wife and I embarked on our entrepreneurial journeys in 2013-2015.

What does this mean for you?

Learn the law of compounding returns. Learn the benefits of low-cost index fund investing. Invest as much money as possible early in your career. Learn tax law and the tax-related benefits of starting a business even if you have a day job. In 10–20 years, if done right, you will find yourself in a position of being able to retire early if you want to.

If you are in debt, that is a whole different ball of wax. Follow Dave’s advice, build a “debt snowball,” and get back control of your life.

7) Save as much as possible early in your career

Someone’s sitting in the shade today because someone planted a tree a long time ago.

Warren Buffet

Finances are so essential to creating a high quality of life that I include a second financial-oriented item in this list!

Read the life-changing book Your Money or Your Life and commit to saving an extraordinary amount of your income, at least 20% and up to 50% of your take home pay. Sound crazy? It’s not. I’ve done it for my entire corporate career. Others have too.

The reason to save a high percentage of your income is the freedom it affords later in life. You can retire early even on a modest salary. How? Save a ton and live a simple life. Saving a lot doesn’t mean you need to be boring, read the next item for more on that!

8) Spend freely on a few things you love

Spend extravagantly on the things you love, and cut costs mercilessly on the things you don’t.

Ramit Sethi

Decide on what makes you happy and spend freely on those things.

Science has proven that spending money on experiences is better than spending money on things. So, try to splurge on experiences. Avoid spending money on stuff (e.g. expensive shoes, jewelry, etc.).

Yet, if you love certain things (e.g. you can’t pull yourself away from those fancy watches), spend freely on them. Just be sure to save ruthlessly on everything else.

I have always been frugal. Even as my income grew to well into the six figures during my corporate career, I spent far less than I earned. I also splurged on things I cared about, mainly travel (I’ve been to 27 countries and dozens of national parks) and donations to build schools and clinics in rural Indian communities through Aim for Seva.

I also splurge when it comes to improving myself through personal development coaching and related trainings. For example, I’ve spent over $100,000 on personal growth, yoga, and coaching over the past 17 years. This investment has been worth every penny.

Decide what makes you happy and go for it!

Cut spending in all other areas and invest the difference.

9) Use all your vacation

My former co-workers never used all their vacation. Crazy right?

It seemed like a badge of courage. At the end of each year, everyone, myself included, would gripe about how much vacation they were “losing.” All the while, we would show a sly grin conveying the mixed emotions of loss and ego. We loved the stigma of being seen as a “hard worker.”

For a while I was proud of working hard and not taking a break. Guilty as charged.

Turns out we were all wrong.

Work breaks are important. People who take breaks end up doing better work. It also demonstrates confidence. Confident people don’t play games to prove how capable they are. If you use your vacation to gather new experiences, that is best. You will come back to work with fresh perspectives.

Don’t let work define who you are. Use your vacation.

10) Master a hobby

Successful technologies often begin as hobbies. Jacques Cousteau invented scuba diving because he enjoyed exploring caves. The Wright brothers invented flying as a relief from the monotony of their normal business of selling and repairing bicycles.

Freeman Dyson

Find a hobby, and spend enough time at it to get good enough to teach it to someone else. You should be good enough for someone else to pay to learn what you know!

Many years ago, I loved to practice yoga and would often go to a yoga studio 5–6 days a week while I was working insane hours. One day, after almost 7 years of practice, I decided to take the leap and become a teacher.

This required significant investment in time and money to complete the training. Making it even trickier, was that I was rising up the corporate ladder in my career. I didn’t think I had the time to teach yoga.

I decided to start teaching anyway. After hundreds of hours of training (and thousands of hours of practice), I taught my first class at a small community center. Some days no-one showed. Other days I’d have a whopping three students!

I ended up teaching over 500 classes over five years, mostly at Shakti Vinyasa in the Seattle Area. I learned how to conduct workshops. I taught individuals and large groups. I taught complete beginners and other master-level yoga teachers. I learned how to modify poses for pregnant women, people recovering from surgery and athletes preparing for big contests. I even played a supporting role in a few Yoga DVDs!

It was a wonderful experience and gave me a strong identity outside of my day job. I found new groups of friends. I discovered new ways to spend my free time (e.g. attending yoga conferences) and even met my future wife through my yoga studio!

My hobby also made a better — happier and healthier — worker.

Best of all, my work never suffered. Instead, I performed even better.

Find a hobby and cultivate it. You will become a more interesting person, and better at your career.

11) Build a broad network of friends

Sometimes, idealistic people are put-off the whole business of networking as something tainted by flattery and the pursuit of selfish advantage. But virtue in obscurity is rewarded only in Heaven. To succeed in this world, you have to be known to people. 

Sonia Sotomayor, Supreme Court Justice

How robust is your network?

Networking events and superficial business deals are not all that useful. What’s crucial is building up a strong network of authentic friendships and relationships. Friendships, like the best business relationships, flourish on trust and rapport. They take care and feeding.

It’s no surprise that the best jobs and careers come not through applications and shuffling around resumes, they come through trust between humans and word of mouth referrals. In the modern era of frequent job changing, this is crucial.

For example, while I worked at my last company for almost 14 years, I had 5 distinct jobs! Each position change happened because someone was willing to bet that I could do the job better than anyone else. In most cases, I wasn’t the most qualified person for the job (based on my resume). Yet, I got the job anyway.

Challenge yourself to forge new bonds. Instead of networking, aspire to connect to people, human to human. Make the goal one of building friendships and relationships.

Broaden your social circle.

12) Do what makes you happy

Q: What is the meaning of life? – Waitress

A: “The meaning of life is happiness. Hard question is not, ‘What is meaning of life?’ That is easy question to answer! No, hard question is what make happiness. Money? Big house? Accomplishment? Friends? Or …Compassion and good heart? This is a question all human beings must try to answer: What make true happiness?” 

-Dalai Lama (see full article)

Is the meaning of life to be happy? I think so.

The tricky thing is, figuring out what will make you happy and how you career fits into the equation.

Remember that what makes you happy one year may not make you happy the next. It is your right to change your mind and change your career. Your family and friends may not understand your decisions, but that is OK.

I started out as a financial analyst. Later I moved on to become a product manager working with engineering teams. Then I became a manager of product managers. Then I became a Director of business planning for one of the largest software products in the world. Then I was a vagabond, traveling the world with my wife.

Now I have built a career as an entrepreneur and coach.

This evolution has taken me decades years.

You might be wondering how to determine what career will make you happy? This is the tricky part, but I discovered three questions that will help you reflect and uncover a few viable choices. Sit with these questions for some time. See what bubbles up to the surface.

After independent reflection, also consider hiring a coach. Coaches can serve as thinking partners and fellow explorers to help you find the signal amidst the noise, and bring clarity to your work. Especially during times of change, or when you are at a crossroads in your work, a coaching partnership can help you unlock your best insights in service of making your future years of work and life the best they can be.


Leave your comment below:

Read on 📚

What I’ve learned this year (2022 edition)

What I’ve learned this year (2022 edition)

John Dewey, an education reformer and philosopher, is well-known for his understanding that learning doesn't come from experience. It comes from reflecting on experience. Being December as I write this, there is a certain nostalgia in the air as the year comes to a...

Bad news and the power of suspending judgment

Bad news and the power of suspending judgment

Michael slipped on a patch of ice getting into a friends car and fell. A self-proclaimed "klutz," taking a tumble wasn't out of the ordinary. This time, embarrassment wasn't the problem. A lingering pain in his wrist meant something serious was going on. An MRI would...

The Friendly Universe Hypothesis

The Friendly Universe Hypothesis

Is the universe friendly, wicked or ambivalent? I posed this question on LinkedIn a while ago and it provoked reactions, some shared in DMs or email, that ranged from "yes yes yes!!!" to "WTF? The universe doesn't give a s@#t about anyone". Responses showed that most...

The Value Of Sabbaticals In A Workaholic World

The Value Of Sabbaticals In A Workaholic World

This very week 7 years ago was momentous for me. After 13 years at Microsoft I took my first prolonged break from work. It was a true "sabbatical" which according to Google is defined as a sustained period of paid leave for every seven years worked. I was overdue by...

What is Coaching?

What is Coaching?

What is Coaching and who can benefit from it? A simple definition of coaching is set forth by the largest coaching industry and professional organization, the International Coaching Federation (ICF): ICF defines coaching as partnering with clients in a...

The Truth About Getting More Out Of Less

The Truth About Getting More Out Of Less

What does it take to achieve more? For most of my life, I’ve lived with an underlying assumption that to produce more, I must do more. If I wish to make more money, I must work more. If I want to be better at a sport, I must practice more. If I want to improve the...