Chris Brogan recently posted a straightforward list of questions to help entrepreneurs evaluate their business ideas. Questions like: “Does it help someone else?” and “Do you know how to promote it?”
It’s a great list. I bookmarked it for future reference, and I encourage you to do the same.
But there’s one glaring omission.
What’s missing is a question that most entrepreneurs (including) forget to ask when starting a business. To be fair to Chris, it’s a question that doesn’t fall directly under the category of “evaluating your business ideas.”
Still, it’s an important question; something you should ask yourself before you launch that new venture. Before you decide to walk the entrepreneurial path at all.
That question is: Am I willing to let people down?
A Leader’s Burden
As entrepreneurs, we’ve steeled ourselves against the financial and emotional costs of failure. We are ready to face setbacks without losing our self-esteem. What we’re unprepared for, however, is how our success or failure impacts those we care about.
This is the reality: when you start something new, you become a leader. And like all leaders, you will have followers who depend on you. Your followers are your family, your friends, your investors, and your customers. People who have placed their trust in you. People who expect you to succeed and who will be devastated if you fail.
Letting people down is painful. I know from personal experience that disappointing someone you care about (or are responsible for) hurts more than the setback itself.
And I don’t think I’m the only one.
When Bernard Madoff’s financial scam collapsed, a prominent hedge fund manager who had lost $1.4 billion of his clients’ money in Madoff’s scheme committed suicide rather than face the people he had let down. Granted, this is an extreme example, but the lesson is the same: don’t start a business if you’re not willing to disappoint people.
Are You Prepared to Let Others Down?
I ask myself this a lot.
If my business flops, will I have the courage to face my family and friends? My investors? My loyal customers? Will I have the strength to tell them that I’m not perfect, that I screwed up, that I was wrong – and then ask them to trust me again when the next opportunity comes along?
I’m honestly not sure what my answer is yet. Are you?
How to Reveal the Risks
Just because you’re prepared to take on the risks of a new start-up doesn’t mean the people counting on you (your followers) are equally prepared. Instead of setting your followers up for a let down, and then having to shoulder all that anger and disappointment all at once, you should help them understand what you (and they) are getting into.
That means at some point, you’ll have to sit down with your followers and talk candidly with them about the possibility of disaster. It’s not an easy conversation to have, so here are a few tips I’ve learned from experienced entrepreneurs:
- Be disarmingly blunt. I think that entrepreneurs as a group are overwhelmingly optimistic people. But while optimism is a fantastic trait, it can easily lead us to sugarcoat situations instead of being honest. When you’re discussing a serious subject like the risk of failure, you owe it to yourself and your audience to be as straightforward as possible.
- Be bold and direct. You are asking someone to trust you and believe in you despite the very real risk of failure – so there’s no point in being shy about it. Trying to talk around the subject only makes you look shady. You have nothing to hide, so come right out and tell them exactly what you’re asking for.
- The sooner the better. Like all difficult yet important conversations, this is something you shouldn’t put off. It’s much easier to explain the risks to someone when things are going well than to blindside them when things start to slide.
- Don’t ask for approval. Revealing the risks isn’t about seeking approval. You don’t need someone else’s permission or blessing to follow your dreams. What you are doing is showing them that you care enough about your relationship to be honest, realistic, and transparent right from the start.
Share Your Thoughts
Are you willing to risk letting people down in order to pursue your dreams? Do you think it’s worth the risk of possibly hurting people you care about? How do you decide? And if you decide to go for it … how do you help those you love and care about understand the risk of disappointment?
Share your insights below.
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Interesting post! I think this question is not a normal one for an entrepreneur, since as you say, we are an optimistic lot.
But to be honest, I'm not entirely convinced of it's usefulness. Does telling people a business might fail, make it any easier when it does fail?
If I spend some time telling people that they might have a car accident, does it make it any easier for them, if their car actually crashes?
Sorry, if I'm being controversial, but thought it might ignite some debate! :)
There is not a single thing on this planet you can do that won't upset someone or tick someone off. Another question is, do you really want to never find out if you could succeed? That nagging question can drive us nuts.
Hey, a little debate never hurts! Thanks for sharing your thoughts (even if they aren't all in my favor). To answer your question, I think telling people beforehand does soften the impact a little bit. I agree that, no matter what you do, failure hurts, and telling people beforehand doesn't mean everything will magically be better. However, I think it hurts worse if you let your family, friends, investors, and customers build up inflated expectations at the beginning.
Does that make sense? Or does it just muddle things even more? What do you think?
That's a good point. I don't mean to imply that we should hold off on our dreams just because they'll upset someone else. However, I believe that we as people naturally don't want to disappoint those we care about or feel responsible towards, and that we shouldn't discount the emotional and psychological impact of letting someone important to us down.
I'm not sure “Are you willing to fail” is the right question you're aiming for, but I understand what you mean. Too often, whether its intentional or unintentional, entrepreneurs fail to really communicate to family, friends, investors, and consumers.
After all, it's bad for business, not to mention embarrassing, to talk about a failing business; and as kaizan mentions, entrepreneurs are an optimistic lot. And yet, in the end, catching people by surprise with one's failures probably hurts them even more.
The very concrete example that comes to mind is the recent collapse on our country's financial industry. So many companies kept an optimistic public face so that when the collapse finally came, investors and consumers were completely caught by surprise. I know that was partially the case with my dad's company.
That's why I really like the four tips you have at the end of the article. A truly good entrepreneur needs to know how to find the right balance between optimism and honest communication.
When you an entreprenuer there is always a risk. You have to handle it in a professional manner and if it indeed fails than it fails but it is of course not an absolute failure because you learn from it. While your supporters be it your family or friends may look at you and feel somewhat of a disappointment…you in the end are the one that should judge and like you said “don't ask for approval” it is entirely up to you. However before getting into the business you have to sit down and face all the situations that will happen in your business and have plans for overcoming such situations…..nice article jeffrey tang
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Jeffrey,
excellent question to ask. And a though one, damn sure.
But that reminds me a bit about the samurais way of living and leading. Face that you will die someday and then go on your way without fear. As long as you neglect or hide from your fears (and hide it from people who trust you) you cannot make the best decisions, because your mind is not free.
If the worst case scenario is accepted all your minds power can be freely used to go for the best.
I see your point, Tina, and I think you've hit the nail on the head when it comes to maintaining customer relations. The other thing to consider, however, is the effect that disappointing other people has on -you-. I'm all for independence and self-reliance, but the reality is that, when you care about someone else (as a customer, a friend, a colleague), letting them down hurts.
That's a good way to put it, Ernest – make your own decisions, but be prepared to face the consequences of those decisions, even if those consequences are social rather than financial.
Fear and denial are definitely two things that limit your potential; the sooner you get them out into the open, the sooner you'll be able to devote yourself entirely to your goals.
I feel like I've been a little unclear in this post, or that I've tried to tackle two related (but distinct) issues at the same time. The first issue is the social impact of business setbacks; the second is honesty and transparency when dealing with yourself and others.
I might have to go back and rewrite this post … or perhaps deal with these two issues separately. What do you think?
I believe the most important thing is to acknowledge to your followers that things may not quickly and easily fall into place with the new venture, but that you are so passionate about what you are trying to do that you are willing to take that chance. You let them know you will do anything and everything you can to succeed and allow them to see your passion for what you are doing. This way, it provides them with an opportunity to buy in and believe in your passion, despite the fact that what you are going to do may also mean you are going to hit some bumps along the way. I think that prepares them for what you are getting into and they are able to be so impressed by your dedication and passion that they understand why you would take the risk. Providing people with a rationale for what you are doing and getting them to believe will make their understanding of your choice that much easier, regardless of what ultimately happens in the end.
Awesome, awesome post my friend.
This is why I love this blog.
A message that I believe everyone needs to hear before getting into entrepreneurship is this ^^
Thanks,
Clément
Jeffrey, your post stirred up a very meaningful line of thought for me.
I come from a long line of entrepreneurs and have been one myself for nearly my whole working life. So I've experienced the results of failure from both sides–as did my father before me.
My grandfather was a farmer and blacksmith. He died suddenly of appendicitis. My grandmother carried on with the farm, but this was during the Great Depression and the farm failed. My grandmother remarried and moved to another state, and she and her new husband homesteaded a new farm. My father never felt that he had been let down by his parents' failure. Farmers were used to failures big and small, farming was inherently unpredictable, and everyone was in it together, supporting each other. That was just life.
As a young man my father started a dairy farm. One day they went out and found the entire herd belly up in a sinkhole. He took it in stride–it was just life. They started over. It was not easy, but it was okay.
Much later in life, he built up a relatively small (about 50 employees) manufacturing business. It did well until he developed Parkinson's Disease. At that point he lost the mental sharpness he'd had, and the business went bankrupt in the next strong downturn.
I had invested time and love in that business, helping out as a teenager and then later. It did hurt when he lost it. But decades later, I'm so glad to have had the experience of working together with him. Those are some of my most precious memories. I learned so much from him. And as I reflect on your article, I realize that maybe the most precious lesson he taught me was that it's okay to fail, and together we can weather whatever happens.
Before I read your article, I'd never thought much about how many generations of entrepreneurs are behind me, and what we've passed down from generation to generation. This know-how about failure was an invisible part of my father's legacy. I'm grateful to be able to see it now, and maybe learn to live from it more. Thank you so much.
That's a very, very good point. Being honest and open in the beginning puts you and your network on the same wavelength, so to speak. You lay out the risks and rewards and allow them to make a decision for themselves. That's powerful – because they are the ones making the decision, it becomes that much more meaningful.
I also agree that passion is incredibly persuasive. Passion in spite of adversity is even more persuasive. Thank you for bringing that up!
Thank you for the compliment, Clement! You've been so supportive all this time; let me know if there's ever anything I can do for you!
Kye, thank you so much for sharing such a personal story. Thank you for being so open and honest. I can't tell you how much I appreciate that.
Learning to fail gracefully, then pick yourself back up is a valuable lesson – one that takes a lifetime to learn. Your family's story illustrates that beautifully. It's also a beautiful example of what happens when a group of people come together with a determined, hardworking, never-give-up mindset.
I think your father was lucky to have such an understanding, motivated daughter. And I'm just as lucky to have met you here online.
Kye, thank you so much for sharing such a personal story. Thank you for being so open and honest. I can't tell you how much I appreciate that.
Learning to fail gracefully, then pick yourself back up is a valuable lesson – one that takes a lifetime to learn. Your family's story illustrates that beautifully. It's also a beautiful example of what happens when a group of people come together with a determined, hardworking, never-give-up mindset.
I think your father was lucky to have such an understanding, motivated daughter. And I'm just as lucky to have met you here online.
I really think the principles of this article can be applied to things outside of entrepreneurship.
I am a very practical person who looks at life from a realistic point of view (maybe too realistic sometimes). When I start any new ventures I always want to have a back-up plan. When I think about pursuing my own dream I think about the consequences of my desires for my family.
Before I had children I didn't think too much about it. I was ready to try anything and to do anything I wanted without thinking of letting others down. Now that I have two kids to care about I do not have this privilege of being reckless. I cannot jeopardize my kids' future and their innocent childhood.
When I was little my dad wanted to pursue his dreams. Unfortunately, he was not a very good entrepreneur and he got into a big mess. My parents had to divorce, my dad had to go work in another city, we have not been close ever since. I do not want to repeat my dad's mistakes that is why first of all I think about people who depend on me and then I think about my dreams and desires.
Jeffrey–Great post. This is the kind of thing we all need to consider and all too often we have our pie in the sky ideas. Doses of reality are definately appreciated.
I don't think there's anything wrong with taking your family's interests and well-being very seriously. You're demonstrating how much you value your family members, and that's wonderful!
The trick is to find a good balance between fulfilling your family's needs and pursuing your own goals and dreams – because you're important too!
I don't think there's anything wrong with taking your family's interests and well-being very seriously. You're demonstrating how much you value your family members, and that's wonderful!
The trick is to find a good balance between fulfilling your family's needs and pursuing your own goals and dreams – because you're important too!
Entrepreneurship is really a big melting pot of big dreams and solid reality. That's what results in such enormous potential for success … and what makes it so much fun too, despite any difficulties or setbacks you encounter. As long as you have prepared yourself and your network for these rough patches, overcoming them is just a matter of time and persistence.
I like how this post makes me think. We all have varying ways that we would answer that one question. Anastasiya is a mother of two, and also suffered the ill effects of her father's failed entrepreneurship. I am a new father of three, and I can tell you that parenthood definitely changes you. It stops being about you, and more about them. For me, I hold down the steady paycheck with the large corporation and I will do so until my side endeavors provide more income that my current job. My answer to that question differs because I don't want my children to suffer needlessly for my failures.
I still do those things I love, and I do in fact make some money at them. I've also built a good income from real estate holdings that I can rely on for several months should I lose my job.
I would like my kids to grow up and see that dad is doing what he loves and making money, just as I would hope to teach them that it is reasonably possible to do so. But I will always have multiple safety nets lying around so that they will never know needless suffering.
If I were single, I probably would have already quit my job and lived off my writing, gigging and real estate holdings. But for me, I have three preemies and a dependent spouse and I'm racking up over a million dollars in hospital charges (seriously, three babies in the hospital for over three months with multiple operations)that thankfully, my employer's health care plan covers, I definitely answer that question differently than the Single, unattached Charley Forness.
Great article, Jeffrey/
Namaste,
-Charley
I will also add that I would never trade that miracle of having my baby triplets for anything. This coming from an admittedly arrogant, reoovered self-centered, anti-family man. I changed and I wouldn't want to change back.
Very insightful…there's a lot of pressure to succeed in the world of entrepreneurial exploits, and things get real when it's YOUR project/dream on the line. There's a fine line between “going for it” and making an “educated guess” here. I think you nailed it by emphasizing communication and honesty. How can we expect results unless we are willing to be honest with each other?
I completely agree, Charley. Having great relationships (like a wonderful family) is incredibly rewarding. I personally don't believe that you're limiting yourself at all – you've simply made a wise, rational decision based on what you value: the health, happiness, and well-being of the family you love. That's a pursuit of values if I ever saw one.
All the best to your triplets! If I can ever offer you any assistance, don't hesitate to ask!
I believe that success is unsustainable if it isn't built on communication and honesty, no matter what industry you're in. And yes, that fine line makes all the difference.
Jeffrey, I'm really moved by your comment. The feeling is mutual.
As an entrepreneur who previously failed a few times, I find that the group that I was hurt most by letting down is missing in your list… The employees.
They believed in my vision, invested themselves, poured their passion into the company, sometimes quit great jobs to join or had made plans for the future. Telling them I had failed them was one of the hardest things I had to do in my life…
Hasn't stopped me though, current company still going and looking good after 7 years :)
(In large part because I learned, and made sure to have backup plans, and take proper steps before it is too late, but I agree that setting proper expectations is quite important)
Whoops, nice catch, Patrick! I suppose I didn't mention loyal, dedicated employees as much as I really should have. Congratulations on the success of your company these 7 years – may you have many more to come :)