• The Big Gulp Newsletter
  • Posts
  • Would You Rather Work for Yourself, Someone Else, or Run the Show? My Hot Take on Each!

Would You Rather Work for Yourself, Someone Else, or Run the Show? My Hot Take on Each!

Author

Charlene Li
March 04, 2024

How can you possibly know if you are on the right career path? If your big gulp moment has led you in the right direction?

🖥️ I’ve worked for corporations. 

🖥️ I’ve run a company.

🖥️ I’ve struck out on my own. 

And I’ve learned so much about what I want—and what I don’t—along the way. 

Here’s what I’ve discovered when:

Working for a Corporation

This is certainly not always the case, but I’ve been very lucky throughout my tenure working within organizations to have truly fantastic employers. It’s why I stayed at Forrester for almost a decade. When I find a good fit, one that provides me with independence, autonomy, and the ability to have an impact, I tend to stay there for a long time. 

The hitch? 

At some point, my cozy home inside an organization became too comfortable. There’s a risk of reaching your growth potential, of running out of new and interesting things to accomplish. There is often a cap on what you can achieve in these settings. I reached mine and never looked back.

Running a Company

In 2008, I founded Altimeter Group, a disruptive analyst firm, and was the company’s CEO. I’ve met many people who aspire to be a chief executive, and I ask them, “Why?”

Money is a common answer. I can tell you 1,000 better ways to make money than by starting a company. 

Control is another reason: “So I can call all the shots!”

That is the worst reason to start—and run—a company. When you’re a CEO, you become beholden to every single employee on your payroll. You are responsible for their livelihoods. It is all resting on you. You can’t do whatever the heck you want: It is the exact opposite. 

For me, the best part of being a CEO wasn’t salary or control. It was working with people who shared the same vision and values. It’s been one of my greatest honors to work with and serve with the people at Altimeter who believed in the work and our impact.

Working For Myself

If you truly want to be completely free—to do whatever the heck you want and answer to no one—you should consider becoming a solo entrepreneur. I for one love being my own boss, but I’m also the first to warn you that it’s not for everyone.

For those who want certainty, structure, and routine, working on your own is absolute hell. 

More than 20 years ago, I took a self-assessment, and the results highlighted two key values: Flexibility and influence. I crave freedom, and I thrive off the ability to make an impact. Money didn’t even make the top 10 list. 

I’m built for my current role of working for myself. 

Still, no matter which piece of my career timeline I look back upon, a common thread throughout them all is that I’ve always been a disruptor and creator. At Forrester, I took on coverage areas just as they were developing, like internet advertising, search, and social media, because I saw they had promise. As CEO, I built a business based on disrupting the subscription business model of classic research firms. And now, my brand of one is built on transformational change—and helping my fellow leaders make their own big gulps. 

Whatever you do, whichever path you take, disrupt. Because the biggest opportunities only happen with the biggest change that you can create. 

— Charlene

P.S. Are you still wrestling with outdated paperwork processes?

What I Can’t Stop Talking About: 

  • Celebrating myself. My birthday was last week, and I celebrated the occasion earlier this month. Whenever friends would arrive at the party, I’d thank them for coming. They’d say, “Well, you deserve it!” My response? “Of course I deserve it!” That catches some people by surprise—my ability to readily receive what someone has given to me. I’ve found that people—leaders, especially—have a hard time receiving. They’re uncomfortable accepting compliments, gratitude, and appreciation. And they’re woefully bad at receiving help. But when you can see the act of receiving as a gift—a beautifully wrapped birthday gift, no less—you’ll start to realize how easy it should be to acknowledge and accept.

  • The excuses we tell ourselves. What’s holding you back from taking on the challenge of AI? If you say that it’s time, staffing, resources, or funding that’s keeping you from creating growth and change, you’re wrong. The only thing holding leaders back is their imagination and their capacity to absorb that change. This is one of the “big gulp” moments I shared with Michael Morrissey on The Next Insights Podcast.

  • My research survey. As someone actively involved in AI in your organization, your perspectives and experiences will be invaluable for the upcoming book, Winning with Generative AI, which I’m writing with my co-author, Katia Walsh. If you your organization has over $100M in revenues, please take our short survey, and you’ll receive highlights and insights available only to participants, as well as a customized benchmark of where your organization stands against other participants. It will only take about 15 minutes and is conducted by the generative AI platform from Outset. Bonus: You can submit voice responses to the questions in any language!

My Latest: 

  • Building your case for disruption. I often say that deciding to take the leap is the hardest part of any big-gulp moment. That’s not entirely true. When you’re running an organization, even after you’ve decided to jump into disruption, you still have to convince everyone else to dive in, too. So, how do you prepare yourself and your team for that inevitable big-gulp? Watch my latest livestream or read my LinkedIn newsletter for our shared insights on how to apply ethics to not only technological innovation but also to your business practices.

  • The biggest challenges facing executives. Leaders are facing bigger challenges now than ever before when it comes to being truly disruptive—and transformational. As a veteran advisor, it’s my calling to help execs sort through them. To learn more, tune in to my livestream, Mar. 5 at 9 a.m. PT / 12 p.m. ET on LinkedIn and Facebook Live.

Thank you to Adobe Acrobat Sign for sponsoring this newsletter.


It's time to uplevel your workflows and ditch the paper chase with Adobe Acrobat Sign. Think beyond just replacing wet signatures – the real power of Acrobat Sign lies in streamlining entire processes. Here's a tip: Consolidate those endless document templates! 

Use drop-down menus and smart fields to customize docs on the fly and drastically reduce errors. This kind of process rethinking not only saves time, but also makes everyday tasks less tedious.

Ready to see the difference? Explore how Acrobat Sign can transform your business. #AdobePartner 


My Upcoming Appearances:

If you are interested in having me speak at an upcoming event or to your executive team, please drop me at note at [email protected]. 

Thank you for subscribing to the Disruption Dispatch, which goes out to thousands of disruptors every other week to help you on your disruption journey—plus a curated recommendation list of a few Good Things I’m enjoying. 

Want more? Check out my weekly publication, Leading Disruption, on LinkedIn.

If you found this note helpful, please forward and share it with someone who needs the inspiration today. If you were forwarded this, please consider subscribing.

Charlene Li

If you found this note helpful, please forward and share it with someone who needs the inspiration today. If you were forwarded this, please consider subscribing.