How To Know Whether to Pursue (or Pull the Plug on) your Entrepreneurial Venture

As an executive coach, I’ve spent nearly 20 years working with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully they can lead with a little more ease.?I work with some of these leaders on my Harvard Business Review Presents?Coaching Real Leaders podcast, where I take you behind the closed doors of real coaching sessions. I also host the?Coaching Real Leaders Community, where I’m joined by an amazing group of leaders and coaches who come together to take a deeper dive into leadership issues.?And in this?Coaching Real Leaders?newsletter, I share takeaways from the many coaching conversations I’ve had over the years. Whether you are a coach or a leader, my hope is that this will help you more easily navigate the challenges you and/or those you coach face.

On my latest @Harvard Business Review Coaching Real Leaders podcast episode, “How Do I Transition From A Corporate Leadership Role to Entrepreneurship?” my guest coaching client is Jane who had recently transitioned from a successful corporate leadership role to starting her own consulting business and was struggling with whether she made the right decision. As luck should have it, several weeks after my coaching session with Jane, I found myself sitting in a 美国哈佛商学院 classroom at my 25th reunion as Professor Christina Wallace led us through an engaging case discussion on entrepreneurship. I was particularly struck by the term she used to describe one of the decisions every entrepreneur must face at some point or another: “pursue or pull the plug”. I couldn’t help but think of Jane in that moment.

High achievers often bristle at the thought of “quitting” on our ventures (yes, I’ve been there myself!). I was curious what Christina had to say about those like Jane who are at a similar crossroad, so I reached out to get her thoughts. I wanted to dig deeper on this notion of "purse or pull the plug" and wondered what questions she thinks an entrepreneur should ask themselves when they are at this decision point. Basically, I wanted to know what she would have asked Jane. Here’s what she shared:

It struck me in this episode how Jane was already thinking ahead to the “after” – after she moves on from her consulting firm and returns to corporate in a C-suite role. Starting her own business isn’t her end goal – and that’s fine! It doesn’t have to be. But usually when I’m talking with entrepreneurs who are debating whether to weather the storm or call it quits the “tell” is if they are still “in it” or if they are already thinking of the “after.” Those who are thinking about the “after” – How will I tell the story? Will folks judge me for moving on? What should I do next? – have just told me that it’s time to pull the plug. Typically, as long as an entrepreneur has runway (i.e., cash) or faith (in the venture, in the team, in themselves) the company will live to see another day. When you have one you can buy yourself enough time to regain the other. But when an entrepreneur runs out of both is when it’s usually time to call it quits. Jane is admitting that she is doing well on the client front, which is no surprise. She’s clearly a top performer (or as you correctly noted, the rare leader who actually leads). So, if she wants to see this succeed, it seems like she has the runway to regain her faith. But, and this is a crucial but, she needs to “choose the vacation she wants”. (I love that phrase!) If this isn’t doing it for her, she’s allowed to move on. It was a season of her career – and seasons end.

It strikes me how we often hear with great excitement the stories of individuals leaving their corporate gig to start their own venture. But we don’t often hear similar stories of triumph when folks reverse migrate back to corporate. To be honest, it’s a notion that has always perplexed me. Why don’t we hear more stories of when the venture didn’t work out the way we thought it would? What Christina had to say about this is so on point!

I think so many people see entrepreneurs as doing something brave, going off to the wild west to build something from the ground up, and that’s a common hero story in America. So, it’s put on a pedestal as something to aspire to. But I want to be clear: there is nothing superior about being an entrepreneur vs. working a corporate job. They are different experiences and challenges and outcomes and therefore suit different people at different points in their lives. I encourage everyone to shift toward thinking of their lives in seasons or chapters. What we want and need and have access to right out of college is very different from what we want and need and have access to when we are starting a family or when we want to dive into a new professional challenge after a decade or two or when we want flexibility to support travel or aging parents or any other number of things that come and go over the 4-5 decades of our careers. There’s no shame in needing different things in different seasons, and there’s no reason not to “rebalance” our career portfolio in the same way we would rebalance our financial portfolio to support change.

Amen to that! There is so much out there about the path to launching your own business. But not as much about how to go back to corporate. So with regards to those who do want to leverage their entrepreneurial journey back into a corporate role, Christina shared some practical tips with me:

When you want to head back into a corporate leadership role from an entrepreneurial one the goal is to share what you learned and how you developed different muscles during that chapter. Whether it’s showing you can build new businesses from the ground up or land big deals or learn about a new technology or industry on the fly, it’s a key part of your story. And anyone who has one eye on what their company needs now will recognize that your entrepreneurial experience is a huge value-add. Because here’s the thing: Corporate leaders of the 21st century have to not only be excellent operators, they need to be creators, and that’s not often a skill set that gets developed on a linear path up the corporate ladder. Sometimes you have to step off and do something completely different to gain that experience, and there’s nothing like entrepreneurship to build your “creating” muscle!

?I loved everything Christina had to say. And I know that many who make or are considering the entrepreneurial leap will still second guess themselves even after reading this. I wanted to know what suggestions Christina had for dealing with that:

Second-guessing yourself is normal, especially when you’ve made a big change and everything is uncomfortable. The question is whether to stick it out for this to start feeling comfortable. And the only person who can answer that question is you. Because there’s no valor in being stubborn. Don’t stay on a path you hate just because you think you should! If you’re second-guessing things because you used to feel like a superhero and now you feel like a novice, you have to decide what you want more: the growth of going from novice to superhero in this new setting or returning to the setting where you can put your superhero skills to work? Neither is better than the other. They are just two different paths. Choose the path that suits you in this season.

?And THAT, my friends, is priceless advice!

Have you second guessed your move to entrepreneurship? Do you have suggestions on how to deal with whether to “pursue or pull the plug” on any career move? Share your experience in the comments.?

Thank you for reading my LinkedIn newsletter! And thank you so very much to Christina Wallace for her massive insights. Christina describes herself as a “human Venn diagram” with a career at the intersection of business, technology, and the arts. She is a serial entrepreneur, an erstwhile podcaster, and a senior lecturer of entrepreneurship at Harvard Business School. Her first book was “New to Big,” which focused on what big companies can steal from startups and venture capital as they think about how to build growth from the ground up. Her newest book, “The Portfolio Life” is coming out in April 2023 and is focused on how individuals can future-proof their careers, avoid burnout, and build a life bigger than their business card by adopting a portfolio approach. You can follow her here on LinkedIn or on Twitter / Instagram @cmwalla

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Catch Jane’s episode ?and all Coaching Real Leaders episodes on?Harvard Business Review,?Apple?or wherever you get your podcasts.?