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The Give & Take of Entrepreneurial Wise Failure

We get ourselves in trouble as creatives when we try to build our presence – that is, in how we promote, market, and brand our work. How we give and take gets us in trouble. What we expect of others gets us in trouble. How we take care of ourselves or not gets us in trouble.

By “trouble” I mean these things can lead to frustration and resentment.

Consider a well-intended email I received recently – and I could give countless other ones. The email came from someone who had called me recently about a project he was developing. A noble project. People had volunteered their time, even expertise. I had never met him. He originally called to see if I would volunteer my expertise on how to raise funds for and launch his project. I had shared with him how I work and that I already offer lots of free services and content. I also led him to a free meet-up I host where he might meet other people and learn how to develop a successful launch. He came to the meet-up, gathered some emails, and within two weeks sent out this email soliciting money to support a potentially noble project.

Here’s what can happen in these instances: We get swept up in our enthusiasm for our creative work – even for a collective project – that we forget that there are literally thousands of other projects and obligations competing for other people’s time, energy, and money.

This person, in my view, had not really earned the right to ask for money from near-strangers – despite the project’s nobleness. The person was promising to deliver something of value in return but had not really done the job, in my estimate, to give value to this group before asking for money.

The person had also presumed that people should be generous with their expertise and volunteer time to make the project a success. In my experience, asking for money from strangers or near-strangers should be one of the last things a creative person does in building relationships or in launching a creative project – especially with and for other creatives. This is similar to an author asking a publishing house to shill out money and costly resources for a promised project.

And I know this person, for a time, was resentful that not more people who verbally supported the project hadn’t jumped on his invitation to send him money.

Several creatives with whom I speak share similar frustrations. How to convey the message of what they offer, how to build an author platform, how to raise more funds for a project, how to get over their resistance to digital technology and online marketing, how to focus on fewer projects at once.

They often feel like failures.

All of these failures are what Tina Seelig of Stanford University calls in her latest book InGenius, “collecting data.” Creative, innovative people and small business owners must put themselves “out there” and risk failing.

There are, though, in my experience wasteful ways to collect data and wise ways to collect data. I’ve spent years wastefully collecting data, but I’ve learned over the past several years how to shift from much less wasteful to more wise. When you frame “failure” in terms of “wise failure” or “wasteful failure” it can shift how you operate in the community, online, or in the world as a creative. What is Wise Failure? 

Trapped in Our Expectations, Blind Sides, and Skill Deficiencies

After so much data-collecting, we can grow frustrated. Bitter. Cynical. People like us who create good work in the world can get caught in our own expectations trap. We start to expect that people should fund our endeavors, should support us. “Hey! I’m doing great work! Why isn’t anyone paying attention and buying my stuff?”

This is where Trouble with a capital “T” comes.

I’ve learned – and continue to learn – to ask,

“Have I earned that expectation?”

“Have I really built an arena of wise generosity that earns me the right even to ask something of someone else?”

“What am I offering that’s valuable?”

“Have I learned the skills necessary to create something that will captivate my audience and make their life richer?”

The self-inquiry doesn’t stop there.

“Have I learned the skills or found the resources necessary to communicate its importance and value?”

“Have I learned the skills necessary to deliver it in a delightful, meaningful way?”

And here is the deal-breaker:

“Am I enjoying the skills I’m learning?” 

Wise Failure

Here’s something to consider. Wise Failure is when we’re not attached completely to outcomes that don’t meet our expectations because we have assumed an intentional, hypothetical, pro-active, and skill-building stance toward our creative work and our presence-building efforts. It’s a winning proposition because we’re going to enjoy learning from the experience anyway. This kind of data-collecting radically differs from “accidental” ad-hoc efforts that more likely lead to attached, wasteful frustration and resentment.

Wise Failure might work with Wise Generosity, both of which might come from these tenets:

1. Identify Your Skill Deficiencies.

If you don’t know how to market your art or launch a fundraising campaign or develop a presence and platform online or locally or write a truly captivating book, then break down the skills necessary to master.

2. Study the Right Resources, Build the Right Alliances, and Pay to Learn.

Set aside time every week to learn what you don’t know how to do that will get your creative medicine out into the world. Study and break down what other people do. Assess what resonates with who you are and doesn’t. Form genuine relationships with people who can help you – not just to take from them but to give back to them.

And if you are only taking expertise from a person, then you might expect to pay for it – especially if you have no pre-existing relationship with that person and you’re in turn expecting people to pay for what you create and offer. It is an investment in your continuing education as a mid-life creative.

3. Give Wisely.

Because creative-minded people are accustomed to floundering with money, many of them feel as if they’ve been generous enough with their time and creations and that now is their time to earn more back. But there’s an art to bring out our natural generosity, of giving – sometimes for free – what we do for people who could otherwise support us.

My original website designer gave me tons of free services – including two days’ full of shooting professional photographs of me here in the valley and in the city. She gave me more time and value than her original estimate. As a consequence, I sent her clients that translated to several thousands of dollars in business the following year. Is that why she gave me so much? I don’t think so. She is naturally generous. Find ways you can naturally be generous and giving before asking and taking.

But I suggest you not give for the sake of giving – or, as my pal Jen Louden tuned me into, “over-providing” – else you’ll burn out. (Note: I’m still learning this lesson.) So give while also getting wise about your own goals for the future.

Graph from Give and Take by Adam Grant (p 185)
Graph from Give and Take by Adam Grant (p 185)

It’s a matter of wise give & take. Adam Grant – yet another under-40 Wharton School professor publishing a provocative book this year – crystallizes what I’ve been exploring in his smart new thought leader book Give and Take: A Revolutionary Approach to Success.

In Give and Take, Grant offers convincing evidence of what factors motivate and contribute to how people give in wise ways – without being manipulative. This way of giving is not reciprocity (expecting a tit-for-tat balance of give & take). This latter point is why I call this kind of giving “natural generosity.” Successful teachers, engineers, entrepreneurs, and others who give successfully – or, I would say, wisely – keep in tact a healthy self-interest while being generous.  Grant calls them “Other Givers” versus the selfish Takers or self-sacrificing Givers.

These categories I’ve found, by the way, are not mutually exclusive. Most of us lean toward certain tendencies in different scenarios. I could identify myself in all four categories at different times, situations, or moments in my life and path.

4. Collect Data.

An ambitious writer gave me an update recently to say that she had “failed” at meeting her writing goal this month. I suggested she treat her writing practice like an experiment. Make an hypothesis: “If I do X for X number of hours/days, then Y will result.”

The same mindset applies to building your presence in the world. Actually, work with reasonable goals – even if you’re not goal-oriented. Test out your efforts. See what lands and what doesn’t.

There’s a lot more to building your presence as a creative than these four points. Knowing how to leverage your native modes of captivating and elevating other people, for instance. Knowing what the Story is that you or your project are about and co-creating with your audiences. Treating it like a wise creative endeavor itself.

I continue to refine and learn as I go, but maybe these four areas will help you get perspective on your own tension points.

There’s also a lot more to learning how to give & take.

Wise Wonder

When you look back on your year of wise work, you want to look back at your best self and say, with confidence, “You’ve come a long way, baby.”

And that long way rarely happens by accident. It’s a look in the mirror with a tad of admiration, maybe astonishment.


What have you learned from your experience with “Failure” – or collecting data? What are you learning about the nature of giving and taking in your creative and entrepreneurial life? Share your insights and stories in the comments section below.

Thanks for running with me,


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    1. Thank you, @jenlouden:disqus . I know your peeps likely wrestle with these matters, too. And you are such an inspiring model of an other-giver. Cheers.

  1. jeff – you always are able to articulate very nuanced points of the creative process that can be elusive. thank you! really helps with seeing what’s blocking my process and how to move forward! susan

    1. Thanks for that feedback. Good to know it’s helping you move forward. That’s what it’s about. Cheers, Jeffrey

  2. Hot damn, man, you spend a LOT of time and thought into these posts. I love coming by your place! Thank you. In answer to your question, I have been “not working” the last couple years as I’ve been focusing on raising the kiddos. I’ve been feeling like a failure of course (no moolah!) but I’ve been trying to keep the finger in the pie by blogging, guest posting, and doing ITRW volunteer work with email marketing. The last week I have been updating my LinkedIn profile and — what?? — it appears that all this “not working” has added up to much more work than I thought. In addition, I was working on a skill I was kinda bad at — online networking and friend-making (Hi you!) via Twitter and such. I have to say that — being a regular Debbie Downer — I was SHOCKED at how much I actually HAD done in the last couple years. It added up.

    I credit Tara Gentile, by the way, who I found via Scoutie Girl blog away back when. She is brilliant at conveying the human business model and living by it.

    I am sure I found YOU because of her so tell her thanks when you see her

  3. I love the model of “wise failure” vs “wasteful failure” — I’ve long been acquainted with the notion of “Fail. Fail faster. Fail better,” but there are still times when failure doesn’t feel like a stepping stone so much as a… well, good ol’ fashioned failure.

    Recently I’ve been working on improving the quality of output on a project that’s been plagued with delays and problems. What’s really been striking is that moving from failure to success isn’t just an intellectual challenge to “figure it out”; making the shift requires a lot of strength and courage.

    The “Wise Giving” concept is very helpful with that. I’d say the majority of “failures” that come to mind, for me, are fundamentally about a cycle of over-committing, failing to keep commitments, and then over-committing again as an attempt to compensate for the previous failure.

    I’ll be thinking about wise vs. wasteful in the coming days and week. Thanks for the helpful insights.