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Would you leave Morgan Stanley to become a blogger?

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Konstantin Sheiko
March 26, 2018

Many people want to quit their jobs, but they are too afraid to make this bold step forward. The “what ifs” are plentiful and the uncertainty looms large. However, world history is replete with examples when certain individuals had quit their careers, only to become successful as a result of this decision.

For instance, Walt Disney was a newspaper editor. The founder of The Walt Disney Company started out as a newspaper editor, but was apparently fired because “he lacked imagination and did not have any good ideas”. Ellen Degeneres was a paralegal and “oyster shucker.” Before being named Showtime’s Funniest Person in America in 1982, comedian and TV host Ellen Degeneres held these two much less glamorous jobs. Julia Child was a spy. The famed chef was not cooking up delicious French cuisines until age 36. Before that, she worked as a CIA intelligence officer. And Harrison Ford was a carpenter – because being a carpenter was much safer financially than acting.

A similar story happened to Brian Kelly. Today he is traveling the world, flying business class, and he is getting paid for doing that too. In 2010, Kelly started his blog, The Points Guy, to help his readers maximize their airline points. It is a pretty regular story so far – but the catch is that Brian had a successful career working for Morgan Stanley – a dream destination for any aspiring financial analyst, broker or investment banker. 

Brian often wrote from his Morgan Stanley cubicle and knew it was time to make the leap from his corporate job after about a year of blogging as many of his colleagues approached him for advice on how to best use their airline miles.

Fast-forward to today, and Kelly oversees more than 20 full-time staff, 50 global contributors, and his platform boasts more than two million followers on social media. Brian has seven tips for those who want to achieve success, making the leap forward into the exciting unknown.

1. Put yourself first: when he first told his boss at Morgan Stanley that he was quitting to work on the blog, his boss suggested he stay for a few extra months. He stayed for a few more months, but looking back, said he regrets the decision and wishes he quit sooner. According to Brian, "huge corporations are not going to look out for your best interests”. 

2. It is never too late to make a decision: Kelly said many people around 2010 were telling him it was too late to become a travel blogger, but he did not listen. Now, he says that he never tells people it is too late. 

Kelly also suggests finding the appropriate platform. "Being a YouTuber may not be the right fit for what you are talking about, but starting a private Facebook group might be”.

3. 'Crazy' means you're onto something: according to Kelly, "When people tell you that you are crazy, you know you're onto something”. He had his fair share of doubters when he decided to work on The Points Guy full time, even including his own mother!

4. A business plan is optional - Kelly's business model changed numerous times during his first few years. Now his revenue comes from web clicks, partnerships and sponsored content from airlines and credit card companies. He recommends to always be open to reiterating your business model and don't think too much about the actual business plan. As for Kelly himself, he has never had an actual business plan.

5. Listening to your gut is important: Kelly’s blog grew after he quit his corporate job, but he still sees any failures as part of the process. "When your gut tells you to do it, just do it. Don't be afraid to fail, just try to do it smartly."

6. Not getting bogged down in details is crucial. Kelly says that the digital age has brought on a plethora of opportunities. In fact, he first bought his web domain for just $10. Kelly recommends not to get bogged down in details - don't think you have to hire lawyers to do everything.

7. And, finally, be a shameless self-promoter. Kelly's Instagram account boasts photos of him riding business class on flights or doing yoga at The Ritz Carlton in Bali, Indonesia. Many of his captions share information on how he was able to squeeze credit out of certain credit cards, in order to find better deals. Here is Kelly’s advice - "People don't want to just see you on their Facebook pages pushing your product," he said. "Help people with what you're trying to do and you'll strike a balance - but you've got to hustle."

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