6 Tips to a Happy Life as a Salesperson

Zen Cachola
ART + marketing
Published in
7 min readApr 4, 2016
Our team surprised our fearless leader, Victoria Spektor, for her birthday.

Within the last 12 months, I’ve closed over $250k worth of deals. And now, I’m living the “4-Hour Workweek” lifestyle and I’ve never been happier.

How did I get here?

After graduating from the University of San Francisco, I joined Yelp as an Account Executive (AE) and spent the next 50 months making 150+ calls a day, building relationships with business owners. In the end, it paid off. I was the first AE to generate $1MM+ in recognized revenue.

Our Team Crushing Quota Every Month

With a $20k quota, I brought in between $50 to $80k every month for 4 ½ years and became the number 1 rep out of 900+ reps worldwide. And I was at the brink of a psychological breakdown.

I’ll never forget the day Yelp went public. We were having a celebratory dinner and all of a sudden — I couldn’t see or hear anything. I panicked!!! I couldn’t breathe and I felt like was going to die. I thought I was having a heart-attack and asked my colleagues to call 911.

The following months were a blur. It wasn’t a heart attack — it was the burnout syndrome.

I lost control.

How I felt on the inside.

Here are 3 lessons I learned the hard way.

Lesson #1: Your instinct is surprisingly accurate — so use it!

When you feel the urge to say ‘no’ to people or situations — do it. You are not missing out — you are making a choice. Whenever my gut questions anything, I listen.

Tip 1: Before you invest your time and energy into a relationship, ask yourself:

  1. What can I learn from them?
  2. What do they talk about most of the time?
  3. When they are telling their story — are they the victim?
  4. Do they insult or judge others?
  5. Do they take responsibility?
  6. Are they cruel to animals?

If the answer to any of these is Yes — walk away. Clearing out dream-stealers was one of my best decisions.

As a millennial when work gets dreary — we hit the scene.

We burn the candle at both ends, go to happy hours, pull late night outings and go to work the next day having had close to 0 sleep.

The result, we get a sick day.

Now let’s see how much it costs. If you pull 2 sick days a month for a year that is 192 hours you are not selling when you could be, which is $9600 you could have made.

This is the price of saying Yes to things you know are not a good idea.

Another example deals with a workaholic salesperson. If you’ve said that you need a vacay 3 times within the last 30 days, you most certainly should.

Block those days or weeks in your calendar, submit the PTO, then choose the destination. Don’t stall, don’t research and don’t make excuses. Don’t wait until you’re burnt out because that’s when you make bad decisions. The last thing you want to happen is to go on vacation and to be too tired to enjoy it.

Tip 2: Hit your quota early in the month. Schedule meetings around your general well-being. Take a week off with your bonus checks, ask for a 3 day weekend at the beginning of every month and ask to work from anywhere in the world once a year.

Lesson #2: Unleash your will-power on things you can control and let go of things you can’t.

If we became sales superheroes, will would be our super power. Luckily for us, we already have it. Some of us, let go of it while others impose it on others. Some people go crazy over the things they can’t control.

Will, when practiced intentionally becomes willpower.

“If today was the last day of my life, would I want to do what I am about to do today?” Every morning for 33 years straight Steve Jobs would look in the mirror and ask himself this question. If the answer was “No” for too many days in a row, he knew it was time to make a change.

Tip 3: Ask yourself this question every day, for the next 30+ years. Include your loved ones. Ask them the same question and enjoy the journey together.

Fretting over things we can’t control is called a waste of time. Taking charge of the things we can control is called will-power.

To become the best at what you do, will-power is a must. Before he became #1, Kobe Bryant would begin his practice at 4am and finish at 7pm. His goal for the day was to make 800 jump shots and he did not stop until he made them.

Tip 4: Do not misapply your willpower on superficial and materialistic things — it can be harmful.

Here are 6 things you can do to strengthen your sales will-power and improve your results several folds.

  1. Listen with the intent to unite and build a genuine relationship.
  2. Slow down your rate of speech and validate others with a thoughtful response.
  3. Suspend your ego by neglecting your need to share — let the other person fully express themselves.
  4. Be a storytelling trusted advisor — educate don’t sell.
  5. Clarify the ‘next-steps’ and reconnect with quid pro quo.
  6. Set realistic expectations of how you’ll meet the customer’s needs.

Tip 5: To sustain improvement, control your thoughts. When a negative thought comes up, shift your paradigm. Replace complaints with solutions, and think about ‘what you want’ instead of ‘what you don’t want’.

Lesson #3: Faith — Complete trust in the process.

Patience in uncertainty is difficult when waiting to get deals signed. If willpower is only 20% of effort producing 80% of result, then 4 out of 5 times I have zero control. Doubt is planted when there’s no control. I have a personal system whenever my faith in the sales process is tested — I learned it from the next startup example.

In a startup culture — one that is less than 2 years old with less than $10k MRR — the sales process will make or break a company.

At Tintup.com, 3 recent grads from USC were able to turn a 3-month old startup into a profitable tech company in the midst of chaos in the Silicon Valley. Investors did not think Tim Sae Koo (CEO) and his team could make it, but the guys kept their faith and chose to raise their “middle fingers to all doubters and decided to take action.”

Inch by inch they iterated on their product, and inch by inch they improved their sales process until they generated $290K in less than 14 months. I was part of this success as Tint’s first sales hire. Here’s a blog post I wrote about the tools we used to turn our sales process into a fun, low-stress revenue machine.

Tip #6: Personalize your alarm clock to unlearn bad habits. What did you not achieve yesterday, that you can achieve today? Put your answer in your alarm clock. When you pick up a new habit, change your alarm to learn something new — every 30 days.

Back at Tint, I began to customize my alarm with aspirations like ‘juice don’t smoke’ or encouragements like “close 3 deals and go home by 3pm.” And it worked.

Today, setting my alarm with thoughtful reminders help me practice kindness. Instead of helping randomly, I’m intentional about helping others daily. It’s the best feeling in the world to be kind.

Suddenly, the 20% of control is meaningless. Work becomes play, life is more colorful and production amplifies without too much effort. Conversations are more delightful. We achieve balance and live patiently with the 80% of things we can’t control. Finally, we can do what we love passionately.

We (salespeople) are not just business agents — who sell. We are human beings who are lucky to be forging meaningful relationships, and that’s the ultimate dance of life.

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