Welcome back to The Workaround. I’m Bob 👋
You’re in good company with fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
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My last three posts share a common theme: companies that lack consciousness and leaders without a conscience.
Funny, I didn’t plan it that way…But if you’ve been following along, I might have motivated you to plot your escape from such a situation.
One common strategy is to seek mental safety and personal growth in a company with a mission—perhaps a nonprofit pursuing a noble cause, or a startup working to improve the environment or provide affordable education.
Maybe a more meaningful company would attract like-minded believers, led by a progressive founder who cares about more than money. Together, this could add up to a job that doesn’t have to be crazy and one that we could look back on with pride at the end of each workday.
Sound good? Well, pause for a beat and read on before you leap…
Based on my experience and that of many others I’ve spoken with, companies that look meaningful on the outside often have some of the worst issues when you sit inside them. For some, it’s like the purpose is an excuse to treat people poorly.
Here, I share four ways good intentions can go awry, why they often do, and how you might recognize or recover from these purpose-based prisons.
My friend Anya graduated from a top business school five years ago. She worked as a consultant for a leading firm for three years. She did well and enjoyed the work, but wanted to fully commit to a business that was making a positive impact on the planet.
Anya took a risk and joined a growing, well-funded startup in the sustainability space in a C-level role. During the interview process, she was impressed by the level of talent among her soon-to-be peers. The Founder/CEO was on the young side, but spoke passionately about his vision for making a big, positive dent in the universe.
She came aboard and was immediately surprised by the company’s dysfunction. There was little organization or direction, and decision-making was entirely in the hands of the founder, who made changes hourly. For the first year, she chalked it up to “startups being startups” and figured that her consulting experience had insulated her from the real world of being an operator.
But by the second year, she realized the company made little progress, and her discussions with friends at other startups suggested that this was much more than the normal level of craziness. Those companies also had more productive cultural norms, while Anya’s company culture played only one note: “You work at an important sustainability startup.”
She also saw how the founder continually used the higher purpose of the company—and his position as the leader of the mission—as a stick to beat his team with. People were fired because he said they “weren’t true believers.” Employees who needed to take a day off when it wasn’t convenient for him were accused of letting the company down. So was anyone who disagreed with his constantly changing mind.
Anya’s story reminded me of something my friend, Jory Des Jardins, told me recently about a company where she once worked. “Culture was weaponized” as managers twisted mission and purpose words to justify whatever decision they made—such as firing people on a whim. Kinda like the devil quoting scripture.
But eventually she woke up to the truth: The founder was an immature leader who hid behind the sustainability cause. She and her teammates were profoundly unhappy, but they continued to come into the office because they believed their efforts would make a positive difference in the world. Anya decided to push one more major project over the goal line, then she made her escape.
Another version of this scenario occurs when the founder becomes so caught up in external adoration that they fail to focus on building the business. Purpose-driven companies and their charismatic founders are fawned over by the press, and industry organizations are eager to put them on a stage. The glow of the stage lights and adoring crowd is addictive, and we can easily tell ourselves a story about how flying halfway around the world for a 30-minute panel might result in just one client or investor. Meanwhile, the team is left grinding its gears at the home office, wondering how to achieve product-market fit.
Something similar can happen in companies in sexy categories like entertainment, sports, and booze. The fun can be a distraction at best, and an excuse to be a dick at worst. A friend invested in a brewery where the founder frequently got high on his own supply, made female bartenders feel uncomfortable, and got into late-night fistfights with customers. One Sunday morning, he received a call from the board chair, who informed him that he had been arrested the previous night—again.
We’re not the only ones to see this pattern. Scott Britton, a startup veteran and now founder of a recruiting service for high-consciouness leaders, posted his experience recently:
I’ve seen a recurring strategy in which founders of meaningful startups are motivated to use them as vehicles for personal gain.
I first came across this one while spending a year at a VC firm that was partially funded by our state. As part of our charter, we worked to steer our investments toward more meaningful industries and underrepresented founders. However, this sometimes enabled a dark game. Here’s how it works:
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The founder announces the launch of a startup focused on a meaningful cause, usually accompanied by a personal, tear-jerking story of how this issue impacted them early in life, and a vision to address the world’s ills. The feel-good tale sucks in significant media attention.
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They raise money from investors who seek more than just a financial return, such as individual angels, family offices, or government-related entities.
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The founder starts collecting a salary, then procures a team and office space. People seem to be busy, but little real progress is made. The founder has an expense account and often uses it for things that fall into the gray area of personal benefit—such as fancy dinners, questionable travel, and consultants who happen to be friends or lovers.
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When the bank account gets low, they generate more media coverage and make bigger promises. The founder states that they are close to a breakthrough, and some major partners are interested. There might even be a pilot project, or a keen-sounding corporate accelerator they’ve been invited to join. Encouraged by the “progress”—but really biased by the narrative they originally bought into—investors write another round of checks.
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Rinse. Repeat…for years…until the investors finally realize there’s no there there. They decline to participate further. Most won’t recognize this was scam-adjacent. Those who do are too embarrassed to speak publicly about it.
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This founder is smart enough to see that the con has been played out. They find a clever way to spin the failure into a success—such as an acquihire or fire sale. They go away for about a year, then come back and run the con all over again with a new idea.
This doesn’t happen frequently, but I’m sure there are a couple of these playing out in your city right now. For clues, look at companies with the most local media coverage over the most extended period of time, and those with the least progress made in measures such as shipped products, customer contracts, and open positions.
Purpose-driven companies can also fail because they can’t live up to the lofty hopes and dreams that got them off the ground.
A sad example of this just played out in the startup scene of my hometown. As described in the reporting here, the founder of a top healthcare startup that was acquired a few years ago experienced the tragedy of his son’s suicide. In response, he decided to launch his next company, Clarigent, which he hoped would develop technology to prevent future families from experiencing what he did.
The company launched in 2018 with plans for an app that used voice and speech biomarkers to detect early signs of anxiety, depression, and suicide risk. And it made a big claim even before the app hit the market: “Measure your mental health in five minutes.”
The combination of a proven, passionate founder and an incredible mission and claim enabled the company to quickly raise $1.6 million in seed funding, as well as secure grant dollars along the way.
The years ticked by, and little progress was made. Media coverage and awards came, but “the next 6 months” became “the next 18 months.” Updates started making excuses about third-party approval or deals lost on the goal line.
Then the data came in: “An Enquirer investigation found that schools and county social workers had no evidence proving that Clarigent’s suicide prevention AI helped them prevent youth suicide.”
And just as the hype check comes due, the paychecks stopped going out. Clarigent went for months without paying employees. One employee was asked to lend the company $200,000.
We don’t know exactly what happened. It seems that startups with the most buzz early on end up dying quietly. Clarigent’s home page is now up for auction. I wish the founder had publicly explained and taken responsibility for the failure, since so many employees, investors, and stakeholders had provided generous support.
Regardless, over-promising your company’s potential impact is another watch out to look for in our and others’ behavior.
This final example is less about leadership and more about the toll that working for a purpose can take on us.
Someone in my circle recently shared his story of interacting with employees of an environmental NGO over several years. He said it was common to see these people get burned out because they were so driven by fear and anger.
Whether it’s an NGO, a political party, or another important cause, these issues are not solved overnight—and sometimes not at all. Hating the other side of the political spectrum or the corporations that exploit, or seeing children dying because they don’t have a cheap mosquito net or enough food, can stress us out and wear us down.
Eckhart Tolle said, “The cause may indeed be worthy, and they are sometimes successful at first in getting things done; however, the negative energy that flows into what they say and do and their unconscious need for enemies and conflict tend to generate increasing opposition to their cause. Usually, they also end up creating enemies within their own organization.”
Even worse, the passionate, energy-draining commitment to a cause often proves counterproductive once we gain more knowledge and think more critically. Consider the people who protested nuclear energy in the 1970s and 1980s, which put a chill on further plant construction. Today, we are preparing to build them again after decades of oil wars and accelerating climate change that decades of clean, safe nuclear energy may have helped prevent.
These are the watchouts, but I’m always compelled to dig into the Whys.
First, it’s “too easy” for these companies to get going.
In most for-profit companies, including startups, investors are hard-core capitalists looking to maximize their returns. The day they write the check, they have hope, but it is balanced by worry—or even a feeling of guilt. So they carefully commit to a tiny number of high-potential companies.
However, when we write a check to a non-profit or fund a meaningful startup, we often experience most of the goodness we expect to feel immediately. You feel great for supporting the cause. Sure, you might hope the money comes back one day, but mostly you want the feel-good to continue. Each company feels like a winner on Day 1.
A founder who receives this kind of feel-good funding doesn’t have the same pressure as one in, say, a boring B2B SaaS business. So they don’t push too hard. If anything, there’s a lot of incentive to keep the someday hope alive for as long as possible.
And there’s a whole ecosystem of enablers that want a piece of your company’s lofty purpose. The awards shows and conferences love to signal that they are purpose-driven by recognizing such companies. It becomes easier and a lot more fun for the founder to take the speaking gig and maybe collect a small grant check to keep the hopes alive, rather than turning it down and facing the high chance that this thing won’t work out, which, let’s remember, is mostly what happens with startups.
Second, these leaders can be seduced and seduce by power.
Just because leaders seem enlightened in one area of their lives—such as choosing a meaningful cause to throw themselves against—does not mean they are fully mature and integrated individuals.
This happens too often with religious leaders and spiritual gurus. They uncover and share a slice of elevated knowledge that attracts people searching for answers. However, for some, this easy adoration triggers shadows in their ego that they have failed to address. They begin to seduce students, denigrate other teachers, and move down the slippery slope to cult status.
Others get God complexes. They attempt to justify their power abuse by taking a page from Steve Jobs and his reality distortion field. Sometimes that works, until karma and hubris eventually come calling. For all of his success at Apple, Jobs’ arrogance also led him to die early because he thought he could cure his own cancer.
Right now, millions of people are working in “meaningful jobs” that are just plain mean. Maybe you’re one of them. The tragedy is that we stick it out because it means so much to us.
We made a significant decision to take a risk and forgo a higher salary to do something that matters in the world. This personal narrative made us feel good about ourselves. Humans are programmed to stick with our stories, and we often suffer from cognitive dissonance. If we reject this company or leader, it’s like we’re rejecting part of ourselves.
So it becomes easier to edit our narrative a bit: The leader is just misunderstood. I’m sure we’ll get funding next quarter. I guess it is my destiny to be a martyr for the greater good.
The first principle is that you must not fool yourself, and you are the easiest person to fool. – Richard P. Feynman
We are also concerned about the social implications of leaving a meaningful job.
Being at this company is a source of pride. Friends praise us for making a difference and love to hear about the good we are doing. We are one of the most interesting people at any party.
It won’t be fun to leave and be forced to explain why we left a company we were once so proud of. No one wants to hear about the awfulness on the inside.
And if we leave the cause, we leave friends and fellow believers behind. We’ve heard how the founder says those who quit are dead to us. And we’ve followed his lead, too, turning on the people who leave because they might force us to question our beliefs.
Like almost everything in life, the key here—and what I’m trying to trigger through this post—is to see that you might be stuck in this purposeful prison of your own design. Once faced with this reality, you might choose to walk out of your unlocked cell.
It’s not fun to hit the breaking point and wake up recognizing that the purpose-driven leader and company you committed so much to was a mirage. I think the feeling is best described in a post by the Flux Collective:
“For those who internalized a sense of loyalty—one explicitly encouraged by the company—the shift lands differently. It feels like betrayal. Betrayal hits twice. The first wound is the act itself. The second is internal: we don’t just question the person or institution that betrayed us. We question ourselves. If I was wrong about this, where else am I wrong? Our footing slips, and we start double-checking everything.”
I’ve been repeatedly inspired by meaningful projects and people with purpose. And on multiple occasions, they turn out to be some version of the categories above. I know it can take a long time to recover from betrayal. I wrestle with it, beat myself up, and write multi-page self-strategy documents on how better to invest my time, money, and emotional energy.
And I go right back to making the same mistake again.
But now, instead of beating myself up, I ladder up and laugh at myself.
I’ll survive the heartbreak that comes from putting my whole heart into what I work on and who I work with.
I’m still going all in on the people and projects that feel purposeful to me, but I’ll let the losses go much quicker, with no regret.
If you are a leader in a meaningful company, be ready for the test of your life…
Power in all its forms—including money, attention, and influence—doesn’t necessarily corrupt, but it absolutely tests us. If egoic fears and desires are still dominant, this powerful energy feeds them until something pops.
“Nearly all men can stand adversity, but if you want to test a man’s character, give him power.”—Abraham Lincoln.
As leaders, we must recognize this and cultivate the character that checks these desires. And character building can take time.
Early in my career, I got an industry publication award for being a “Top 50 Marketer.” Back then, I aspired to receive that award one day. I built a relationship with reporters, partially in hopes of being recognized. I was thrilled to receive it eventually. I added it with pride to my resume and loved including it in my bio for speaking events.
More recently, I was given an award I didn’t ask for, and honestly didn’t want to accept. I guessed that they probably picked me because the decision-makers know me. Once you’ve been on the other side of picking award-winners, you see how the sausage is made. I would rather it go to someone who would have appreciated it more, or whose skills are under-recognized. I also didn’t like that it recognized just me for work that our whole team was responsible for. I ended up accepting the award with genuine gratitude, but did my best to credit our staff and made a point to emphasize this was our award, not mine.
I don’t dislike the ambitious young me who was striving for personal recognition. But I’m glad the twists and turns of life helped me grow beyond this and enabled me to build purpose-driven companies that are even more special on the inside.
You deserve the same. Keep putting your heart out there until you find it!
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A little something I found meaningful. You might agree…
To Profit or Not to Profit?
Sandhya Domah is a founder of a startup with a purpose, and she writes on Substack in part to share the early decisions her team is working through. Recently, she wrote about the pros and cons of building a purpose-driven company in either a for-profit or non-profit structure.
In the post, she walks through a comparison of Patagonia (for-profit) and Mozilla (non-profit).
If you like the topics I cover here, you’ll also enjoy Sandhya’s work. Head over to Re-Imagings and click that subscribe button!
To profit or not to profit?
I believe that the biggest vehicle for change in the next few decades isn’t necessarily going to be government or policy, but grassroots movements and business…
4 months ago · 4 likes · 4 comments · Sandhya Domah
