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Cherlyn Chong: “It’s never going to be one size fits all”

It’s never going to be one size fits all. Any mentor who pretends to listen to your needs yet still insists on the way they do things, or is so arrogant that they don’t see the obvious flaws in their business plan, doesn’t actually care about you. I’ve had mentors like that, and it was […]


It’s never going to be one size fits all. Any mentor who pretends to listen to your needs yet still insists on the way they do things, or is so arrogant that they don’t see the obvious flaws in their business plan, doesn’t actually care about you. I’ve had mentors like that, and it was incredibly disappointing. They ended up costing me more emotionally, financially, and energetically in the long run. Understand that your personality, appeal, offer, and even audience will be different, so find a mentor who truly gets that.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Cherlyn Chong. Cherlyn is the founder of Steps to Happyness, where she is a breakup recovery and dating coach for high-achieving professional women. Currently living between California and Singapore, she serves an international clientele, helping these ambitious women succeed in their love lives the same way they do in their careers.


Thank you so much for doing this with us! Can you tell us a bit about your childhood backstory?

Sure! I was born and raised in the city-state of Singapore, with my mom, dad, and sister. I always was a bit different from my peers, in that I never wanted to behave in the “right” way or do things the “normal way,” probably to the silent horror of my parents.

While pursuing the Asian dream of getting a prestigious degree and a lucrative career so I could earn lots of money, I quickly decided that working myself to death wasn’t quite my cup of tea, and begun to plan my way out before I landed my first corporate job.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah-ha” moment with us?

It’s interesting, I actually had to get my heart broken. My last job wasn’t working out, and I was thinking about pursuing something online. And then my ex dumped me over the phone, and I just about had it with life. In a moment of blatant defiance, I thought, you know what, I’m going to turn this pain into something good instead of evil. I have a degree in graphic design, so I drew a comic about my heartbreak while I was undergoing it in real life. The thing got onto The Huffington Post, now Huff Post, Upworthy, Lifehack, and many other platforms. In the span of just a few days, more than 12,000 people visited my site. That was the moment I knew I had something that people were interested in.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

The one thing I did that changed everything was listening to people who were a lot more successful than I was. I love taking the fastest, least painful way to success, and hiring people who knew exactly what they were doing and could stop me from making a fool of myself was the best thing I’ve ever done.

Also, having a fantastic tribe full of smart people to bounce business ideas off is priceless. I swear, the investments I’ve made for some of my programs were already worth it because of the access to these people.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

This will be unconventional advice, but if you’re afraid that your hobby or idea won’t take off, you might be right. One person can do really well, while another might struggle in the exact same niche. It really depends on your personality and what you’re doing to achieve your goals.

So first, ask yourself why you want to pursue this for a living — what will it really get you? Where will it take you? How many people do you want to influence or inspire, and why?

Then, if the reasons genuinely fire you up, the next question is, will it fly? Find your courage and test it. No one can tell you if it will work, the only way you’ll ever know is when you test it on a small audience to see if it’s viable.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

One of the best things I’ve done is to stop speaking to everyone, just to a select group of people. Because those people tend to be action-takers with high integrity and a willingness to learn, they get amazing transformations in a very short span of time.

You dread things when everything becomes wearisome and unsatisfying. Having such ideal clients means that when they constantly succeed, I do too, and my work became very rewarding.

I’m all about efficiency and speed, so it’s incredibly exciting for me to see what they can accomplish, which gives me a lot of pride in what I do.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I love the fact that I can run it from anywhere with a decent internet connection. One of the reasons why I started it was because I knew that I would find a partner overseas, and would need to have the flexibility to move and work whenever I wanted.

That did happen, which makes me even more grateful for the business.

I also love connecting with movers and shakers and amazing people with brilliant ideas. It’s rarely dull.

The downside is that entrepreneurship is a lonely journey. I can’t even share it with my partner who has a regular 9 to 5 job.

You’re your own boss, but you’re also the only one responsible for how fast your business takes off, and some days it’s hard to motivate yourself. It helps a lot to have accountability buddies with whom you can set goals, and who bring similar value to the table.

Also, your fashion style degrades; I have many smart corporate dresses that I will never wear, to my dismay. That’s a first-world problem, and I haven’t solved it yet ha ha!

Can you share what was the most striking difference between your actual job and how you thought the job would be?

Certainly. I didn’t know it would be so emotionally triggering. There are many limiting beliefs to overcome, such as feeling like a fraud, not being good enough, feeling like you’re ripping people off, etc.

I thought it would be smoother sailing once I got a viable service out there, but the truth is, you don’t ever stop getting out of your comfort zone.

No one really talks about how taxing it can be if you speak to people who are the wrong fit, or how scary it is to put yourself out there, so when reality hits, it hits you hard.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Oh, many times. I simply reminded myself of one starry night when I was in corporate. I had stepped out of the office building, looked up at the sky and wished I could just run away.

The pain of entrepreneurship can never rival to how I felt back then, and it drives me forward on my darker days.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Back in 2015, I had just acquired 2000 people on my mailing list, and I had sent out a single email inviting them to join my 15 dollars beta-test course that was launching in 1 week. I was so new, and even asking people to pay me 15 dollars was a huge stretch for me.

I was so disappointed to find that only 5 people signed up, and I lamented about that in a post that got lots of attention in a popular Facebook entrepreneur group.

Then, more and more people signed up closer to the launch date, and I was able to start the course with 18 participants. I can’t believe that I had made such a big hoo-ha about my “failure,” only for it to turn out to be a success! My lesson is to always wait to confirm because announcing these things.

Who has inspired or continues to inspire you to be a great leader? Why?

I am always so inspired by Marie Forleo. Her image is so fun yet elegant at the same time. She’s such a great interviewer, and I love how she treats everyone — I believe that’s why her team always seems to be so passionate about her mission.

How have you used your success to make the world a better place?

I find myself being a lot more generous. I give more and help more. When you’re coming from a place of abundance, it’s so much easier to give freely and influence the world.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Hire a GOOD mentor. Like ASAP.
    It’s not fun to constantly figure this out on your own. I turned a year of 1000 dollars months into 5000 dollars months by hiring my first mentor, and it went up from there.
  2. It’s never going to be one size fits all. Any mentor who pretends to listen to your needs yet still insists on the way they do things, or is so arrogant that they don’t see the obvious flaws in their business plan, doesn’t actually care about you. I’ve had mentors like that, and it was incredibly disappointing. They ended up costing me more emotionally, financially, and energetically in the long run. Understand that your personality, appeal, offer, and even audience will be different, so find a mentor who truly gets that.
  3. People are not going to like you. Accept it and speak to the ones who do.
    I’ve wasted a lot of time agonizing over what I did wrong to piss people off, when in actual fact they were always going to be angry no matter what I did. So it’s better to move on quickly and focus on the people you’re meant to serve, who do want to be your fans.
  4. Start building up a media presence as soon as you can.
    Authority is everything but like, takes time to build up. Amazing clients tend to hire the best, so make sure that you present yourself as the best. A solid media presence helps so much in building up your credibility, and if you’re a coach, your client comes pre-sold before they get on the phone with you.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would absolutely love to start a movement that educates people on toxic relationships. It annoys me to no end that we’re taught things like math and chemistry but not useful life skills.

We have so much shame around toxicity that even your best friend might be in a toxic relationship and you would never know. I want people to know that once you decide to be free of a toxic person, a whole world opens up for you. There is so much more space in your life for everything else.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“I’m not OK, but I will be.”

I came up with this quote when I announced that my ex and I were no longer together on my Instagram. It doesn’t deny how I was feeling back then, but I’ve also given myself a way out at that moment. I’ve already told myself that I would survive this, and therefore I would. So simple, but so powerful.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Without a doubt, Marie Forleo. It would be such an honor to have lunch with her and talk about her vision for the world. I swear, that woman can do anything, she even bartended and taught hip-hop dance before her business took off.

She gave up a very prestigious career at Vogue to pursue her dreams, and that reflects the time when I, too, gave up my career at a Fortune 500 company.

She is so charismatic and funny, one of the rare people I see who has made it big but remains so genuine. I would love to do an interview with her — she has already interviewed many of my favorite people. I sound like such a fan-girl! But really, I would be happy just sitting next to her, soaking up her funky boss babe vibes.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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