10 Questions To Ask Yourself If You Want To Quit Corporate Life & Be Successful

Published in

The Startup

7 min readAug 12, 2018

“I wish I had the courage to live a life true to myself, not the life others expected of me.” — Bronnie Ware, The Top Five Regrets of the Dying

A summer’s beer in London is always a good excuse for a catch-up. And I recently met up with some ex-work colleagues. They’re successful, high earning, investment professionals working in the ‘City’, London’s equivalent of Wall Street.

And no doubt so would I be like them, if I’d stayed in the City. But I have no regrets about giving it up to become a professional speaker and writer.

How many times have you considered leaving the corporate world to become a creative professional, launch your own business or join a startup but found reasons why it’s not the right time? We can always find excuses but there are some serious questions you need to really think through before you make the leap.

1. Do You Really Know What You Want To Do?

“Whatever the mind of man can conceive and believe, it can achieve.” — Napoleon Hill

A rare lucky few know from an early age what their calling is or fortuitously stumble into the right profession. However, most of us haven’t been given the chance to figure out what our ideal life or career could be.

This is because Western society took us down a rigid path of education and careers. As kids, we were forced to make quick decisions about what to study and then were pushed into the rat race without experiencing different professions. So how could most of us possibly know what our ideal career is?

And, how do you now find out what that is? The answer is to experiment. For example, if you like painting and you think you could make a living from it, get it out there and see if others think the same. Instagram could be one way to showcase your art. If you love food and think running a restaurant could be your passion; during your next vacation arrange to work in a restaurant for free. Or if you still don’t have a clue, why not do what I did — take some time out to travel and discover yourself.

2. How Long Can You Wait?

“I’ve just got a mortgage/married/pregnant…next year when I’ve saved.” -Anonymous

Of course, there are some important milestones in life we need to provide for. And if you’re young and working in an environment where you’re given early responsibility — learn and take advantage of it. But don’t fall for the myth that it’s never too late. Life is finite.

According to scientists, we’re the only species that know this, yet we rarely live our lives like it’s going to end one day.

I’m in my 40’s and I can reasonably expect to live for another 40 years. That sounds like a lot of time to learn the craft of motivational speaking and writing. But if I break that time down into days — I only have 14,600 days left (40x365). Tomorrow 14,599!

3. Do You Have An Income Problem Or An Expenses Problem?

“Too many people spend money they earned..to buy things they don’t want..to impress people they don’t like.” — Will Rogers

The fear of sacrificing your income today for a future reward is very scary for some. Often though the problem is not earning enough, it’s that you’re spending too much.

Work out what your basic living costs are and compare it to your current income. Perhaps you’re spending much more than you need to?

Do you have an income or expenses problem? Figure that out and you’ll be halfway to making your decision about leaving.

4. Does Your Career Make You Feel Successful?

“You’re winning in the wrong game.” — Michael Serwa, #1 UK Life coach

I was a very good investment analyst; so my former colleagues and associates told me. But it wasn’t my true calling. As Michael, my former life coach suggested: Like many of his clients who feared the transition, I was winning in the wrong game.

If you find your job stimulating and feel you still have many goals to achieve, then you’re probably not ready to go it alone.

But being successful in your career isn’t necessarily an excuse for not trying something else. If you’re a high salary earner and you’re not happy, almost certainly you’re ready to make the leap.

5. Do You Shy Away From Responsibility?

“The price of greatness is responsibility.” — Winston Churchill

You may be making big deals, managing a large team or perhaps trading millions. But you work in the 9–5 environment and when you go home you can leave it all behind for the day. But when starting out, usually it’s just you doing the actual work, marketing and strategising etc.

How good are you at self-management? Does it scare you the idea of having all the burdens of your new venture on your shoulders?

Your actions will have a direct impact on your success. Does that sound like fun to you?

6. Are You Prepared To Surround Yourself With New People?

“You’re the average of the five people you spend the most time with.” — Jim Rohn

Many seek comfort and security in the familiarity of their work colleagues and friends. And because of ‘tribal mentality’ encoded in human DNA, it feels very hard to move onto new tribes.

But if you’re to succeed in your new endeavour you’ll need to become the best you can at it. That means learning from others who are already successfully treading that path. Are you ready to spend much less time, or even, ‘move on’from your old colleagues and friends?

I wouldn’t have made half the progress that I have, if I hadn’t made efforts to spend time with and learn from some successful authors.

7. Can You Change Your Habits?

“The harder I work the luckier I get” — Gary Player

I’ve never met a successful person who doesn’t work hard. But that doesn’t mean sitting at your desk and slogging the hours away. In fact, I’ve heard through a friend of a friend that Tim Ferris (author of The 4-Hour Work Week), is one of the hardest working people they know. But if you follow him, you’ll know his efforts mostly relate to continual self-improvement.

To commit to your dreams is to try new ways of doing things and being open-minded about change. And this involves making mistakes and constantly evolving.

If you like the routine and structure of the office, you need to ask yourself if going it alone is right for you?

8. Does Your Partner Understand Your Dream?

“It has to be a true partnership, and you have to really really like the person you’re married to because it’s a hard road..I think you go through that wonderful love stage, but when it gets hard, you need a little bit more.” — Michelle Obama

We’re all responsible for making our own dreams a reality, but naturally, it will be easier if your partner is emotionally and psychologically supportive of it.

Will they understand if you leave your job? Will they resent that suddenly they may be the main source of household income?

If you have a partner, it’s imperative to communicate your ambitions and be prepared to make some compromises.

9. Do You Want To Leave The Corporate World Because You Want To Be Rich Or Because Of Your Aspiration?

All I know is to write what is personal to me. I don’t know how to write a bestseller.” — Richard Paul Evans, #1 New York Times Bestselling Author

Innovators want to innovate; writers want to write. Did Bill Gates sit down and work out how to be a billionaire? No, of course he didn’t. He chose his passion before the money.

If you want to be rich for riches sake, it probably won’t happen, because you won’t have a devotion that keeps you going through the tough times.

Ask yourself why is it that I want to do this? If it’s your truth and you want to create, it’s for the right reasons.

10. Are You Prepared To Commit To Your Dream?

“And when you want something, all the universe conspires in helping you achieve it.” — Paulo Coelho, The Alchemist

Life is challenging and rarely is someone an overnight success. We never see the hours successful people put in and sacrifices they make.

Do you want to give up the generous office perks: holiday entitlements, healthcare, expense account, bonuses and the clear promotion path? And what are you prepared to cut out: Netflix, social media, the pub, i.e. the things that are incongruent with your goals?

In other words are you ready to absorb yourself into your new business? Or as Coelho would say, are you prepared to ‘fight the Good Fight’ — that is to really engage in the daily battles of success and failure so that it slowly compounds into knowledge and the heroic win over time?

If you’re enjoying my posts and want to support my efforts to break free and make a living my way, I’m partial to coffee (and a glass of wine in the evening😉). You can visit me here to shout me that coffee, and from there, also learn about my books and other projects.