| Works for Me |

“How Do I Go from Broke to CEO?”

Friends are encouraging me to open a business, but I don’t even know where to get started

I’m 23 years old and really need advice. I’m at my first job, and I’m finding it really boring. I know I’m young and this is going to sound silly, but I look around and see all these wealthy, successful CEOs, and I feel stuck. I know the standard advice to people like me looking to get somewhere in life is to start at the bottom, but I don’t see how my job will ever get me anywhere. I’m tempted to look for a new job, but I wonder if I’ll feel the same way in another position. 

I didn’t do well in school, but was always told that my skills will help me in the business world. I’m really driven, and people have always assured me that I’ll make it big one day. Friends are encouraging me to open a business, but I don’t even know where to get started.  

How do I get to the next step?

 — Broke to CEO

TO quote a mentor of mine: “Do you know how long it takes to become an overnight success? At least ten years.”

Seeing people so far ahead of you can be either inspirational or challenging — it’s your job to choose.

Personally, I enjoy listening to interviews about famous people and how they achieved success. My trick to gaining from those talks is:  a) to filter closely for wisdom that resonates with me; and b) to remember that I’m not looking to copy someone else, but to gain inspiration from them. Recognize that no one else has the exact template for success that will work for you.

The pattern that I enjoy seeing in stories of successful people is this: They started with something they enjoyed, excelled, and then grabbed an opportunity that came their way and made the most of it.

What’s interesting to me is that I don’t think they were necessarily presented with better opportunities, but that they were more likely to see possibilities and try more things.

I think the first thing you need to consider is what your natural skills are, and if this job capitalizes on them or not. You’re definitely more likely to be successful if you enjoy what you’re doing, and you’re more likely to enjoy what you’re doing if it uses your best skills. That’s step one on your ladder to success.

It is important to temper satisfaction at a job with the recognition that there are going to be some parts that you absolutely don’t love about your job — any job — and that’s okay. Then there’s also the pressure you feel to know that you are doing something, anything, to move upwards in your career. Do remember that when it feels like the elevator isn’t coming, the smartest thing to do is take the stairs. They may seem slow, but they always get you where you need to go, and make you stronger in the process.

You’ve shared a bit about yourself and what others think of you, and it seems you most likely have an entrepreneurial streak. You probably have a higher-than-average risk tolerance, are curious, and have strong interpersonal skills. It also seems that it’s important to you to achieve some public recognition or level of success.

Let’s explore this a bit more deeply: When you say you want to be a CEO, what exactly do you really want? To be the boss? Make lots of money? Have all the headaches? Be famous? Figuring that out will clarify what your goal really is, so that you can make sure that the work you do today and in the coming years aligns with that goal.

Most importantly, remember that you are, and always will be, the CEO of your life — and it’s up to you to make it a good one.


Shaina Keren is a career consultant who helps people discover and create careers that fit their best talents, interests, and life goals. She also advises businesses on hiring and keeping “the right people in the right seat,” in a win-win approach to growing businesses and careers.


(Originally featured in Mishpacha, Issue 938)

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