Deep Thoughts

Why you don’t have to ditch corporate life to be successful

I cannot tell you how tired I am of seeing the same article over and over again about why I should quit my 9-5 job.

It seems like everyone and their grandma is an entrepreneur, solopreneur or the next great startup CEO telling us to quit the 9-5 or escape the rat race. It’s popular, but that doesn’t mean it’s right for you.

Many of us find a great deal of success in working for others. When Simon Sinek spoke about his famous golden circle and why you do what you do, he wasn’t only referring to your why. The concept covers contributing to others ‘why’ too.

Plus, if we all decided to become entrepreneurs, solopreneurs and independent workers then our economic landscape would be in a bit of trouble.

It’s becoming all too popular that everyone is now a lifestyle expert or coach or life hacker or whatever random title they have this week. Everyone is so keen to tell us that we shouldn’t work for someone else and that they have a fancy article with a list of all the things successful people do and if we do these, we’ll be successful too – I don’t buy into that.

TV gif. Conan O'Brien dramatically breaks down in tears of agony and screams, “Whyyy.” His face is red and glistening with streams of tears. He then crumbles into himself and hangs his head low in complete devastation.


Simple, it’s not the full story, and a lot of those who preach this message are not succeeding in this game themselves. They’re preying on what is the obvious connection on most social media platforms – selling a lifestyle you wish you had without the hard work.

Success in the obvious path

In fact, there are many successful people who have built their careers and found fulfilment in traditional jobs.

Bill Gates, the co-founder of Microsoft, worked a 9-5 job for years before starting his own company. Ursula Burns, the former CEO of Xerox, worked her way up the corporate ladder over the course of 30 years. Warren Buffett, one of the most successful investors of all time, has spent his entire career at Berkshire Hathaway.

Not convinced? Here’s even more:

  1. Mary Barra, the CEO of General Motors, has spent her entire career at the company, starting as an engineer and working her way up.
  2. Jamie Dimon, the CEO of JPMorgan Chase, has worked in the banking industry for his entire career.
  3. Tim Cook, the CEO of Apple, worked at IBM before joining Apple.
  4. Indra Nooyi, the former CEO of PepsiCo, spent over 20 years at the company, working her way up from a junior executive to the CEO position.
  5. Sheryl Sandberg, the COO of Facebook, worked at Google before joining Facebook.
  6. Lloyd Blankfein, the former CEO of Goldman Sachs, spent his entire career at the investment bank, starting as a commodities trader and eventually becoming CEO.
  7. Ginni Rometty, the former CEO of IBM, worked at the company for over 30 years, starting as a systems engineer and eventually becoming CEO.
  8. Satya Nadella, the CEO of Microsoft, has worked at the company for over 25 years, starting as a member of the technical staff and working his way up to CEO.
  9. Reed Hastings, the CEO of Netflix, worked at a software company before starting his own company, Pure Software, which later merged with another company to become Rational Software. He later joined Netflix as CEO in 1998.

Each of these people found fulfilment in the world of traditional careers.

We often hold each of these people as examples of success, but don’t highlight their accomplishments were gained in what we deem as the obvious career path. Take solace in that.

Side hustles + traditional careers 🤘

Over the last decade, we have seen the rise of side hustles as a powerful add-on to our traditional careers.

No one job is going to make you feel fulfilled 100%. This is where side hustles can prove useful. They open a door to explore other pursuits, learn new skills and drive a sense of purpose.

Side Hustle Definition

A job or occupation that brings in extra money beyond one’s regular job and main source of income.


Working a traditional 9-5 job can often provide stability, a regular income, and a sense of routine (or that’s what we tend to believe, at least).

Yet, it’s normal to feel unfulfilled or stagnant in this type of work. We’ve all been there. One solution to this is to explore side hustles, which can offer you the opportunity to learn new skills, pursue passions, and find a sense of purpose outside of the traditional 9-5.

Side hustles can take many forms, from freelance work to creative pursuits.

The beauty of side hustles is the opportunity to gain experience in areas that may not be available in your day job. This is exactly why I created my weekly newsletter and blog, Steal These Thoughts!, and this publication you’re reading.

Let’s unpack an example, someone who works in finance may find also fulfilment in photography, writing, or design. A side hustle in this space can allow them to indulge in those passions. By exploring new skills and interests, you could find renewed energy and purpose in your work life. Again, something I can vouch for!

Some find side hustles can offer a sense of control and ownership that may be lacking in a traditional 9-5 job. Great for those who feel stifled or limited in their day job.

Another unforeseen benefit I found and I’ve heard from others is the sense of community and connection that may be missing in a traditional 9-5 job. Pursuing a passion project can connect you with others who share similar interests and values. This could lead to new friendships, collaborations, and opportunities that may not have been possible otherwise.

A number of you reading this have connected with me because of my side hustles.

Research from automation software firm, Zapier found nearly 40% of Americans have a side hustle on which they spend less than 10 hours a month.

In summary, side hustles are cool. You can have a 9-5 and a 5-9, it doesn’t have to be one or the other.


  1. Many people find success and fulfilment in traditional careers.
  2. Side hustles can be a powerful add-on to traditional careers, offering the opportunity to learn new skills, pursue passions, and find a sense of purpose not always available in the 9-5.
  3. Not everyone wants to work for themselves.

Before you go… 👋

If you like my writing and think “Hey, I’d like to hear more of what this guy has to say” then you’re in luck.

You can join me every Tuesday morning for more tools, templates and insights for the modern L&D pro in my weekly newsletter.

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