Predicting the Future

More often than not, when we’re predicting the future, we think something along the lines of:

“Because I feel like this now, I’m sure that I’m going to feel like this later.”

 This is the biggest trick our mind plays on us, based on the fallacy that there’s some inexorable link between my today experience and my future experience, whether that future is next week or next month.

The relationship between these two things is almost nonexistent, but this simplistic, misleading thought is the source of countless cycles of stress and worry.

As in:

“I feel stressed and overwhelmed now, and things are only going to get busier, so I will surely feel more stressed and more overwhelmed in a month’s time. And I won’t be able to handle that.”

There’s a reason why every athlete’s post-game/match interview is so unrelentingly boring, when they talk about “I just tried to approach the match one point at a time, and I kept fighting until the end, knowing it wasn’t over until it was over.” The only answer is to have this moment be this moment, and the next moment be the next one.

Today I feel the way I feel today.

Tomorrow I will feel another way.

If a strong pattern emerges that connects these two things, and it’s a pattern we don’t like, then by all means we need to make a structural change.

But a few days when we’re dragging can become an unbearable weight if we convince ourselves that the way we feel now is the way we’ll feel forever.

We’re terrible at predicting the future, so the best thing to do is to stop pretending otherwise.

The Fallacy of Long-Term Career Goals

I’ve always been terrible at setting long-term career goals. To start, I never knew what I wanted to be when I grew up (outside of maybe a veterinarian, because I loved animals). That felt like a profound shortcoming to my 10-year old and 20-year-old selves.

Partially this was because the list of “grown up jobs” that I’d heard of was absurdly short: teacher, doctor, lawyer, fireman, policeman, musician…maybe architect on a good day.

But the real problem was the half-baked notion that this process works from the outside in.

Done properly, it’s the other way around.

I know I’m in the right job if I’m thriving and learning, if I’m creating things of substance that I believe in, and if I’m working with great people. That’s the whole enchilada.

If you’re finding it hard to find all those things at once, that’s OK. Start with great people and find a way to work with them. The rest will follow.

And, if you’re wondering what I mean by “thriving and learning:”

Thriving is doing your best work. Work that makes you stand out, work you get lost in because you’re in the zone when you’re doing it, work that people keep noticing—whether in how you show up or what you delivered. Pay attention to this praise, especially if it’s for things that come easily to you. That is the kernel of you at your best.

And learning? It’s self-explanatory, and it should be non-negotiable. It is, and always will be, the only path to growth.

Words are Branches, Thoughts are Roots

My face has always been pretty easy to read. Indeed, my wife occasionally tells me that she doesn’t like how I’ve reacted to something, to which I’ll reply, “but I didn’t even say anything!”

“Ah, but you were thinking it.”


We all have versions of this, the non-verbal cues that we communicate irrespective of what we do or don’t say.

The question then arises: when we discover that we’re not showing up how we’d like to the people around us, when we learn that their experience of our non-verbal, energetic responses to them aren’t what we thought they were, what do we do?

Maybe, we think, we should change the words that we say.

Do we feel timid? We can say something confident.

Are we often quick to contradict? We can stay quiet for longer.

Have we been finding a colleague frustrating? We can complement him.

Do we secretly know that we’re not up to this new stretch assignment? We can talk the talk.

All of that is a start, certainly. In fact, often it works to behave our way into new attitudes, not the other way around.

But we can also fall into a root/branch trap here, and never claw our way out. When this happens, we let ourselves off the hook of digging into the underlying thoughts that are what’s really going on.

Where that fear comes from.

That judgement.

The avoidance of a courageous conversation with that colleague.

The skills you believe you don’t have that you so desperately need.

To create real and lasting change in how others experience us, we must begin by observing, with intent and curiosity, where our root thoughts come from. We must bravely drag them out into daylight and see them for what they are.

Then, slowly, slowly, we start chopping away at the roots of our habitual responses.

Without doing this work, we end up hand-waving in defense of the words we said (or the micro-expression that flashed across our face), instead of acknowledging the work we still have to do on the underlying thoughts racing through our minds.

Speaking of which, we’re turning the page to yet another low point in American politics. It seems like soon we will all be discussing whether the President of the United States said the n-word, and then surely, if he did, watching smokescreen discussions of why “it’s just a word” and how we are all overreacting.

Let’s not forget that the real conversation isn’t about the word, it’s about the thoughts that lead to it.

The real conversation is the unspoken truth of the ugly, hateful, dehumanizing root thoughts that give rise to those words, roots that are indefensible and immoral.


Vision, Strategies, Tactics, and Results

We each have a natural set point, a place we feel most comfortable.

We might be seers who can imagine, out of whole cloth, a future.

We might be doers who need to be neck-deep in the work to come to conclusions that mean anything to us.

We might be analyzers who see the whole field of play and can visualize which pieces need to be moved in what ways to tilt the field.

We might be movers who just need to make something happen to feel any sense of accomplishment.

The point is, each of us starts somewhere, and like any good journey the first step is to figure out where that “where” is.

For example, I remember back in college the terror of each paper I had to write.

Inevitably, days before a paper was due I’d stumble across one classmate or another whose answer to a perfunctory “so…what are you writing about?” came back in fully-formed, immaculate, intimidating paragraphs. I’d nod, mutter something in response, and walk away, even more stressed that I was still just reading, and reading, and reading some more, taking tons of notes but struggling to come up with any sort of well-formed ideas of my own.

Over time I discovered that my own process required me to read and sit and write and struggle and read some more until, finally, my perspective would emerge. Not an easy process, but once I’d done it enough times I noticed that I like starting from the middle and working my way up (big picture) and down (specific proof points or tactics). No coincidence, then, that having a daily practice of capturing and developing ideas—in this blog and in my daily work—is part of how I structure my time. It’s a system that allows me to produce my best ideas.

So, if, irrespective of where we like to start, we must eventually build out everything from vision to tactics and all that lies in between, we must ask ourselves questions like:

How do I process information?

Where do I feel most comfortable along the chain?

More often than not, what are the moments, contexts, or situations in which my new ideas arise?

Once I’ve got a new perspective, or insight, or even just an inkling, what steps do I then need to take to fill out the other pieces of the puzzle?

And, finally, given all of this, how can I structure my day, my time, my conversations (or lack thereof) to give myself more opportunity both to develop the nuggets that come most easily to me, and to then turn these into flushed-out ideas that I’m ready to start putting out into the world?

Individual and Institutional Fundraising

Over the past six months, a greater proportion of the fundraising I’ve been doing has been institutional rather than individual. By “institutional” I mean fundraising from people who have been charged with donating somebody else’s money – whether or not it’s a formal, recognized institution (e.g. a large private foundation, a corporation, etc.).

In both individual and institutional fundraising, there’s a strategic element and a people element. The strategic conversations are around goals and outcomes and what success looks like. The people element is around what motivates a person to take action – the story and the emotional elements that move people to act, as well as the interpersonal dynamics that are always at play.

The one thing that is missing from these institutional conversations, which easy to miss if you’ve not experienced it directly, is a deep, personal element. In my experience, real, substantive conversations about real, substantive philanthropy nearly always get personal: they touch on motivations, hopes and fears, aspirations, and legacy.

These conversations require something different from the person doing the fundraising: a comfort getting into that murky space where they, too, are more open, honest, and vulnerable than would ever be expected in a purely professional context.

My hunch is that the reason most people don’t wade deep into individual, big-ticket fundraising is either because they don’t understand how deeply personal these conversations have to be, or they are unwilling or unsuccessful at going there. This means that if you have the courage to take that leap, along with openness to do the real work that this leap requires – to learn about yourself, to understand your own motivations for doing this work, to help people talk about their own purpose – you’ll soon be part of a very small group of people willing to take it to another level. This path is a heavy lift, a long walk that requires emotional labor and has the potential for a serious personal and professional payoff.

Of course your other option is to sit safely at a desk replying to yet another formal request for proposal, hoping that your program will be the one out of 1,000 that’s picked out of the pile.

This is one of the greatest blend-in or stand-out opportunities in the nonprofit sector.

Your questions grow up with you

Do I want to be a superhero or drive a firetruck?

Do I want to be a teacher, a doctor, a lawyer or a veterinarian?

Do I want to be a salesperson, an entrepreneur, an investment banker or a professor?

Goldman or Morgan? TFA or Robin Hood? Charter school or public school? Facebook or Google?

Until, eventually:

What kinds of problems do I want to solve?

How much direction do I need?

And how much do I want those around me to need?

What kind of approval do I seek?

Do I like creating new things or polishing others’ great ideas?

Do I work best with people who are highly structured or more free form?

Do I thrive or crack under pressure?

Do I want a workspace that is quiet or loud?  Open or closed?

What happens when I’m in the spotlight? What should?

How do I manage my time to be most effective?

How hard can I work in a sustained way?

Am I a starter or a finisher?

Do I process information best alone or in groups?   In conversation or in writing?

How important is culture to me?   Values?

What does leadership mean to me?

How do I make others shine?

Where blog posts really come from

One of the reasons I blog is so that I have a regular, disciplined practice of turning loosely-formed ideas into concrete, cogent, shareable posts.  Over and over again.  Until I get better at it.

Part of the power of repetition is getting to observe a process unfold repeatedly.  So, over the last 5-plus years of blogging (and of life), I’ve learned that most of the time my best ideas come through conversations.  When someone asks me a great, thorny, interesting question, and we engage in real dialogue about how to answer that question, I learn things.  This is a powerful piece of self-knowledge that I otherwise wouldn’t possess.  It informs how I structure my time and how I think about the conversations I need to have, and the people I need to interact with, to learn, to push my own thinking and my own understanding of the world and of my work.

Rare, though, is to have a photograph of that moment.

The most popular post I wrote in November was How do I get a job in impact investing?, and after I wrote the post I saw this tweet from Josh McCann.  It’s a photo taken the moment I was asked by the Warton Social Venture club how to get a job in impact investing. I was stumped, but I winged it, and we talked, and together we figured it out.

How to get a job in impact investing

Where do your best ideas come from?  Alone, or in conversation?  After a lot of reading and study or on the spur of the moment?  With a pad of paper and a pencil, a whiteboard, with a cup of tea or cranking at your desk at work, constantly jumping back to your Facebook feed (probably not)?

We all struggle with managing our time the right way.  Knowing where we get our best ideas can help.  This is one of the big ideas in Peter Drucker’s Managing Oneself, an article that’s worth rereading at least once a year.

When I grow up

It wasn’t until three or four years ago that I figured out what I wanted to be when I grow up. Not what specific job, not each twist and turn of my career. The characteristics of a job that is right for me: my strengths, where I shine, where and how I can deliver value to an organization.

While I’d feigned clarity and direction in countless prior job interviews and graduate school applications, I felt like I didn’t know in any real way where I was headed. I knew I’d been good at school, and since graduating college I’d managed to figure out a lot of things I didn’t like. But I still had a pretty limited affirmative understanding of what I was put on this earth to do.

No doubt our educational institutions are a huge part of the problem. Even in graduate schools, which are meant to prepare students for the next stage in their careers and to help them get there, I spent 99% of my time “learning stuff” and 1% of my time trying to figure out who I was and what made me tick. That can’t possibly be the right balance, yet that’s how nearly all of these programs are structured. (Sure, part of this is on me. I made the mistake of thinking Business School was school when it didn’t need to be.)

I can’t overstate how many incredible people I meet who have no idea what they’re supposed to do with their lives.

So, first and foremost: it’s OK that you don’t know. It takes time.

Second, this notion of figuring out exactly what you want to be when you grow up is an anachronism. It’s time to dispense with the preschoolers’ notion of careers (doctor, lawyer, footballer, firefighter) which is pretty much the only mental model we all have. Instead, the work begins with exploring questions like: what am I best at? What things seem really easy for me that are difficult for others? When do I shine? What kinds of problems do I like solving? How much uncertainty makes me comfortable/uncomfortable? How much recognition do I need? From whom? Why? How much do I like risk? Am I more conceptual or concrete? Do I love ideas or execution? How am I at building relationships? Am I creative? Do I like to teach others?

I think we knew all this stuff once, and we forgot it.

A short story: weekends in my house are a juggling act bouncing between three kids. Yet last weekend I managed to get a few uninterrupted hours with my 8-year-old son, and I’d told him we could do anything he wanted. While all the kids in his class would likely use that time to play soccer or baseball (and yes if I’d let him we’d have played video games), his idea of a perfect afternoon was to go to a craft store, buy a box of popsicle sticks, a package of pipe-cleaners, a piece of green foam, a piece of Styrofoam, some Elmer’s gel glue, and, as a bonus, a packet of fake moss, and then spend a few house building a model playground from scratch in our basement. Voila:

I have no idea what my son is going to be when he grows up, and I don’t suspect that he’ll know that for a while. But I know that he gets joy out of creating things and out of using his imagination. It engages him fully. In some way and in some form, he’s going to have to make stuff if he’s going to be really happy.

That’s the only level at which I’ve been able to figure out what I’m meant to do in the world. It’s not a shingle I can hang on the door or a defined career in any traditional sense of the word. What it is is a first-time understanding of who I am, of what the organizations I’m part of seem to need from me, of roles I continually find myself playing whether I choose to or not.

Slowly, the outline started to form, and once I saw that initial outline, my job was to keep trying to get the picture into sharper focus. Still lots of work to do – a lifetime of work – but it feels a lot easier than groping around pretending that I’m supposed to fit myself and my career into some little box I first heard about when I was a little kid.

There are fewer and fewer boxes out there, and you probably don’t want to fit into any of them anyhow.

Peter Drucker – Managing Oneself

A little while ago, a colleague of mine sent around Peter Drucker’s Managing Oneself article from Harvard Business Review.  He described it as “something to read and re-read over time,” and having read the piece a few times now I’ve put it on my “reread this one annually” list.

The whole piece is about self-knowledge, probably the most important lever in sustained and longstanding professional and personal success.

From the opening, just to give you a flavor of both the content and Drucker’s direct, no-nonsense writing style:

History’s great achievers – a Napoleon, a da Vinci, a Mozart – have always managed themselves. That, in large measure, is what makes them great achievers. But they are rare exceptions, so unusual both in their talents and their accomplishments as to be considered outside the boundaries of ordinary human existence. Now, most of us, even those of us with modest endowments, will have to learn to manage ourselves. We will have to learn to develop ourselves. We will have to place ourselves where we can make the greatest contribution. And we will have to stay mentally alert and engaged during a 50-year working life, which means knowing how and when to change the work we do.

Most of the article covers, with incredible clarity, topics you might expect: how to know your strengths and build on them; understanding your weaknesses; the power of real and honest feedback; etc.

But then out of left field Drucker spends a good chunk of time saying that it’s crucial to know if you learn best by reading or listening (apparently General Eisenhower was a reader,  President Lyndon Johnson was a listener).  Huh?

This pretty much stumped me, both because I’d never thought about it before and because, after thinking about it some, I had no idea whether I was a reader or a listener.  I assumed that since I read a lot and write a lot that I have to be a reader.

It turns out that I was wrong.  Here’s how I figured it out.  A few months after first reading the article I found myself preparing for a big presentation and wanted to include a discussion of a newer Acumen Fund investment.  I’d read piles of pages about the investment and had tons of information, but I just wasn’t feeling comfortable.  Then I sat down for 30 minutes with someone on our team to discuss the investment and everything changed.  I felt the texture, I could grasp the nuances, it clicked.

Turns out I’m a listener.  I’m pretty sure that having figured this out will have a big impact over time.

One final gem from the article that just made me smile – the kind of thing you don’t expect from a management guru:

Manners – simple things like saying “please” and “thank you” and knowing a person’s name or asking after her family – enable two people to work together whether they like each other or not. Bright people, especially bright young people, often do not understand this. If analysis shows that someone’s brilliant work fails again and again as soon as cooperation from others is required, it probably indicates a lack of courtesy – that is, a lack of manners.

Hope you enjoy the full article (“Best of HBR”) as much as I did.

What’s sacred about you?

Here’s the one thing I can’t stop thinking about after writing yesterday’s post: what’s sacred about me?

Meaning, Jonathan Haidt’s research tells us that to understand people and how they make decisions, you have to understand what they hold sacred.  Around these sacred beliefs, there’s a halo of willful ignorance, one that few facts can penetrate and, if they do, these facts fail to dislodge the core belief.

It must be the case that this applies to self-image, that there are things I fundamentally believe about myself (that you believe about yourself) that blind me (you) to the facts.

The capacity for change comes from the willingness to observe the things that are most dear in my self-image and expose them.  Most obviously, Jonathan challenges me to look at the notion that I’m an open-minded person by asking me how much I understand the perspective of people whose core beliefs differ fundamentally from my own.  More broadly, we all walk around with notions of who we are, namely…

I am:

[   ] good

[   ] bad

at public speaking; writing; analysis; closing a sale; inspiring others; leading a team; coming up with new ideas; getting things over the finish line; fundraising; meeting new people; taking risks.

For example if you’d asked me when I was 23 what job I would never, ever want to or be able to do successfully I would have said “any kind of sales job.”  Whoops.

There are only two ways to break this cycle.  The best way is to decide not to listen to the stories you tell yourself and to start doing things that contradict your most sacred beliefs about who you are and what you’re best and worst at.  Then supercharge your efforts by creating a culture of honest and open feedback (a la Open 360) – a work environment in which people who know you and who deeply care about your success and that of your organization actually sit down and tell you what we’re best at.

I promise, you’re your worst critic.   In the act of trying, buttressed by feedback from invested and caring colleagues, you’ll show this critic who’s boss.