The Hardest Question for an Exited Entrepreneur to Answer

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Go to any social event - be it a business conference or the family picnic after your child’s softball game - and you’ll eventually be asked: “So, what do you do?”?

The question is partially asked out of curiosity, and perhaps also a way of determining your socio-economic caste in society. We’ve all been asked it so many times that we all have our pat answer.

Once this exchange is complete, with both sides sharing their “what do you do” script, the conversation can then move on to other topics, like weather, politics, sports, and popular culture.

But what happens when you ask someone what they do and the response is simply: “I do nothing.”

This prompts a second question, which is usually something like “Um, what?,” to which the response might be: “I sold my company and left so I don’t currently have a job.” This then moves to question three, shifting from present-tense to future-tense: What are you going to do? Often, the answer is unpolished and rambling: “Um, well, uh, I have this idea around hotels and how it would be cool to have a hotel with a chocolate theme but, uh, I don’t really know anything about hotels and so it’s just an idea right now. And if anyone you know needs some consulting help, um, I’m doing that too.”

The Grand Narrative of $uccess

Rick Elgenbrod notes in his fantastic book, What Happens When You Get What You Want? , that this third question comes up after the completion of a life event: “You sold your company, quit your job, graduated from school, survived cancer, inherited some money, got divorced, got married, dropped your kids off at college. What are you going to do?”

Our society places a lot of importance on productivity. We respect people who are doing something. People who aren’t are PIPs - previously important people . Elgenbrod refers to this as the “Grand Narrative of $uccess: “The “lesson” it teaches is that our lives should be dedicated to being successful, and that as long as we’re pursuing success we’ll have a place in this story and be valued.”

This has been drilled into our minds from a young age. We’ve heard inspirational quotes like “an idle hand does the work of the devil,” or “success is 99% perspiration and 1% inspiration,” or ”you can sleep when you die!” Heck, it’s even part of the history of the United States: it was the Protestant Work Ethic, after all, that drove our country’s success, right? We were so obsessed with working harder than everyone else that it became a religious belief!

The consequence of this ongoing societal pressure to ‘do something’ means that someone ‘doing nothing’ is either met with contempt, pity, jealousy, or a combination thereof. Elgenbrod argues that we eventually have to choose between two paths: staying true to the Grand Narrative by always striving for more money, success, and status, or creating our own path.?

It is far easier to follow the Grand Narrative, for two reasons. First, because it is the accepted path. No more awkward conversations at parties! And second, because the Grand Narrative shields us from looking inward and answering the tougher questions, like “Who am I?” “What Do I Care About?” and “How Can I Live My Best Life?”

The Entrepreneur’s Dream

I talk to a lot of entrepreneurs who tell me that their dream is to someday sell their company. When these entrepreneurs think about their post-exit life, they envision never having to worry about money again, having the freedom to do whatever they want, and having the stamp of approval from their peers (and probably their parents, and maybe people who picked on them in high school!).

All of this can be true and I don’t blame anyone for striving for these goals (I certainly did). That said, after hearing these goals, I like to turn the conversation on its head and comment: “What a lot of entrepreneurs don’t realize is that selling your business is selling your purpose and identity for cash.”

This can manifest itself in two ways. First, for an entrepreneur who is mission-driven - who really believes in the business he is building - selling suddenly takes control of that business away from him. At the end of the day, a buyer can tell you with great conviction that they are totally aligned with your vision for the future, but once they are in charge, they have the right to change their mind, and quite often will. And sometimes that new vision includes marginalizing the founder. When mission-driven founders see the direction of their business change or are pushed out of their business, having the financial capacity to buy a new Lamborghini usually doesn’t compensate for the hit to their purpose and identity.

The second unexpected consequence of a sale is that it may force the entrepreneur to rethink what his actual purpose and identity is. When you are building a business, after all, you are living the Grand Narrative of $uccess. After you’ve sold it, you either need to find a new business to grow (and re-enter the Grand Narrative) or go down path number two and find a purpose and identity outside of being a productive business builder.

Deciding on Your Own Terms

Each day that passes after the entrepreneur stops being part of the Grand Narrative, the pressure increases on the entrepreneur to rejoin the narrative. Taking the summer off after a big exit - that is totally cool and admirable (decompress before you go hard on building your next thing, buddy!). But if it’s been two years since you sold your company and you are still doing a lot of meditating and pickleball and not a lot of “success’ing,” people start to look at you askance. The What are You Going to Do question arises more frequently and perhaps with a bit of disdain.

I suspect that the hardest thing to do is to conclude that your purpose and identity are driven by something very un-entrepreneurial, like volunteering every day at a food bank, being a stay-at-home parent, or writing poetry. Being able to know that this is your true narrative and not care about what others may think is truly reaching self-awareness.?

Heck, maybe the billionaires we should be admiring are not the ones giving 10% of their net worth to charity but the ones that have found contentment just living life (and maybe giving more like 95% of their net worth to charity, but that’s a topic for a different article). Imagine Jeff Bezos announcing to the world that he’s going to spend his time caring for foster kittens. Society would laugh and perhaps criticize him - a man with such genius, who can wield such influence on the direction of the world, spending his time with kittens - what an outrage!? But if that’s what truly brings him contentment, perhaps that is the sort of person who is the best role model society could ask for.

Whatever you do, don’t bow to pressure from others to rejoin the Grand Narrative. You may very well conclude that you want to start another business because this really brings you purpose. I am certainly not saying that it is wrong to participate in the Grand Narrative. The key, however, is to make this decision on your own terms and timeline. To consider the alternative paths and make an informed choice after you have thought about all of your options.?

This likely means having a prepared answer for the What Are You Going to Do Question which is short and sweet: “I don’t know and I’m good with that.”