To Find Purpose in Your Work, Start Small

Finding purpose in your work is not nearly as easy as commencement addresses would have you believe.

For me, it used to be the bed test: Do I jump out of bed to get after it? And do I go to bed bone-tired but satisfied from doing it? Or would I rather be selling mattresses?

But meaning gets deeper yet fuzzier in middle age, when competence gives way to significance in our priority list, and we wander around asking big, vague questions like, ‘Is this the life I wanted?’ and ‘Am I really going to bed at 9pm’?

Rottweiler And Leash

Why is “the why” so important?

Viktor Frankl answered that question pretty clearly (and before him Nietzsche) in Man’s Search for Meaning where he recounts life as a prisoner in a German concentration camp and how having meaning was the best chance at survival. He then covers his method of psychology (Logotherapy) that revolves around purpose.

This is the bible of why we need a ‘why’ and one of my favorite books. It’s also one of the best “you think your life is tough?” reality checks to read while you scarf down your latte and gluten-free muffin.

“For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s personal dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself.” – Viktor Frankl

But damn, that’s hard to find. And stressful if we don’t find it, especially with all the pithy online inspirationoise telling us to follow our dreams.

Providing for one’s family is enough for a while, but at some point it’s not just about a paycheck when there are other opportunities to meet our basic needs.

I’m aware that ‘professional purpose’ is not a problem that plagues farmers in Nepal. They know their why. But our country is obsessed with it. And with good reason. Without purpose, as Frankl wrote, we get depressed, addicted and aggressive. Our inner lives become a zoo with open cages.

My Experiment

Last time, I tried to hack purpose by pledging half the money I made towards causes I cared about. That helped, but turned out to be too peripheral if I didn’t enjoy the daily grind.

This time, I’m jumping into stuff I love (“following my curiosity” as Elizabeth Gilbert TED’ed about) and hoping it ends up in purpose. And if not, at least I’ll enjoy the ride.

Perhaps purpose is always there, but gets drowned out by all of the useless voices in my head. Instead of being my co-passenger in a nimble sports car, purpose has been quietly reading a book in the back of a school bus full of obnoxious kids.

I’m still a work in progress, but I’m picking up a few things.  

I feel closer to my purpose when…

  1. I get past my own whiny crap (I save that for this blog) and help others. It’s a Hallmark-worthy sentiment, but it’s true.
  2. I have a healthy mix of childlike joy, where I lose hours without noticing, and adult responsibility where I feel like a part of the tribe. I’m like that triumphant-faced dog going for a walk while carrying his leash in his mouth.
  3. I give up trying to cure cancer. I can make a valuable impact on people’s lives doing what I love and being a good person while doing it.
  4. I don’t worry about what others think. This is an easy thing for me to list as a self-help bullet, but profoundly difficult work. Will dig in here in a later blog.
  5. I crave the results. Yes, the journey is the destination, but without a fierce desire for the endgame, the work doesn’t feel as vital.
  6. I am surrounded by people who give me energy, who push me and make me laugh. It makes the ditch-digging parts okay.
  7. I just start doing stuff. The “What Color is Your Parachute” tests are interesting, but jumping in and doing the work is more enlightening.

The Result? 

Well, it’s not like Indiana Jones using his staff to find out where to dig. It’s more like a kid discovering a big, open playground near his house. By opening myself up to curiosity, I found a bunch of new places to play for awhile –  “life experiments.”

Just breathe. Start small. Follow my gut. Find good people.

And then occasionally I step back from it all.

And I’m reminded that maybe I’m relying too much on my professional life for purpose. Like a lot of Americans, I’ve been consumed with one section of a jigsaw puzzle that is much larger than I imagined.

As Frankl writes, we also find purpose in the love we have for others and in how we give meaning to our suffering.

I love my work, but maybe the process of finding purpose there is what leads us to other parts of that puzzle that we never would have discovered.

And that’s all good work.


The Key to Changing Yourself: Embracing Limbo

Mosquitoes were feasting on us. Dusk was flirting. We were sweaty, hungry and ready to call it quits. When we started the hike early that afternoon it was all laughter and TV theme songs. But spirits had since declined to murderous looks and mumbled obscenities.

Sophomore year in college I did an Outward Bound course in the Everglades. And halfway through the 22-day program of canoeing through alligators and bumping into manatees, our teachers left us to navigate eight treacherous backpacking miles from a pristine beach to a remote, decommissioned airstrip – the only flat, dry place on the island to camp – using plastic compasses and bandanas on sticks. Not an easy task. Kind of like hitting a three-pointer from the stands.

It was clear we were lost. Our newly-minted orienteering skills weren’t up to snuff. I wanted to go back to the beach and eat gorp.

Going through life transitions feels like that: a long, uncertain slog that doesn’t seem to go anywhere. Going back to the safety of the known is tempting.

Processed with VSCOcam with a6 preset

I’m in that transition stage again. And it’s as hard as I remember.

I know I need a change. But getting to the “new you” means navigating through a dark forest full of fear, doubt, identity issues, practical and financial considerations, and the gravitational pull of your old life. And there’s not even a plastic compass.

In short, limbo sucks.

Life Transitions

Big life changes come slowly (midlife, kids growing up) or hit you like a gut-punch (getting fired, losing a loved one). Or you could just be cleaning your gutters when some inner-voice tells you your life isn’t working.

There’s a great book called Transitions by William Bridges that describes the process of life changes. I’m over-simplifying, but the basic model is:

  1. Death of the old self: Often after an incident (good or bad), we are forced through the emotional train ride of letting go of the old life/self/ideas.
  2. Neutral Zone (the creative stage): The limbo state where we lick our wounds and ask what the hell just happened while slowly understanding our new potential.
  3. Rebirth of the new self: Sometimes without even noticing, our new life takes shape with new energy and focus.

The big challenge for most people is getting stuck in this middle stage. We get scared and want to go back to the known – our pretty little beach with snacks. Limbo means loss of identity, and that’s frightening. If we’re not that person anymore, who are we? Just a ghost in a void. (And if you’re like me, an annoyingly chatty ghost who talks about the struggle with anyone who will listen.)

So we retreat to our old selves in an effort to belong and be on familiar ground again. “This identity worked for me before, so I’m sure it will again.”

It’s why our country loves plastic surgery and trophy spouses – we can’t seem to stop trying to be 27. But that identity no longer serves the same purpose and mostly leads to more pain, and 45-year old men dressing like extras from Jersey Shore.

My Misstep

Doing this last startup was “grasping for the old me” – it was the comfortable enterprise-software-CEO identity, and the team was even in Portland. I got halfway into the Neutral Zone, got scared, and jumped back under the warm blankets of old Dave.

Problem was, that identity isn’t me anymore. I’m still entrepreneurial, but where I get my energy from has changed dramatically, and being in a different location from the team was terrible. Plus, I no longer own khakis.

I don’t regret it though. I had to do something. And I felt what it was to go back to the old. The important thing was to keep moving. Stasis was much more painful. It’s why I now have a (for some reason 80’s-styled) plaque in my office that says, “Keep Making Decisions.”

keep making decisions

It was also important to be open. It’s like that joke about the guy who is looking for his lost keys under a random streetlight he’s never been to because there’s more light there. I was looking for clues in the wrong spot. When I removed those limited assumptions, it became more of a scenic hike with panoramic views and no tourists with selfie sticks.

Speaking of hiking, back to my 19-year old self….

After another hour of drudgery, it was my turn up front with a bandana on a stick to mark the sight line. At that point, I was looking longingly at tree branches as potential beds.

I finally got about 75 yards ahead of the group and stopped to mark the line. In order to get my placement though, I had to move out of the way of a man-made sign that read (I kid you not), “Please Stay Off the Runway”.

I was so tired and convinced we were lost, I wrote off the sign as random human detritus in the forest. I was literally standing on the runway but couldn’t accept it. I read what the sign said to the group because I thought it was funny and they exploded with high fives and hugs. I was confused for a good 90 seconds until it finally dawned on me that we might actually have made it.

Going through a transition again, it’s clear that life is a lot more tasty when I embrace the process fully – to get past the fear and love limbo, to go from bashing myself in the head to enjoying my own company, being open to whatever and to just keep going.

Not only is the destination worth it, but it turns out the hike is pretty sweet if you can keep singing. And you can leave the khakis at home.


Why Being a Remote Startup CEO Doesn’t Work: My RipFog Story

I spent the last year trying to incubate a company in Portland from the Bay Area. It didn’t work out. It was not a unicorn (more of a gremlin). But it’s all good. Here’s the story.

Some of you may recall that, out of desperation, I set a timer for myself to start a company. My recent attempts at finding work had failed the passion test. The critical voices in my head were causing me to crack. My brain was like the stoning scene from Monty Python’s Life of Brian.

I wasn’t convinced doing another startup would be ideal, but it was movement. And staying busy is a good hack to keep the demons at bay.

Having grown a company in Portland back in “the naughts,” I knew a lot of really talented people up there. And they were all in the market for something more interesting to work on. My thought was that we could build a product in Portland, and find the people to sell it here in the Bay Area. Ergo, the name RipFog: Rip City (Portland) + Fog City (SF). For 98% people however this become RipFrog, even if they were staring directly at the written name. Apparently frogs are linguistically dominant.

So when one of my old architects from my previous company in Portland had an idea, we jumped on it. It was a brilliant, highly-technical idea, and way out of my sweet spot. But bumbling my way to knowledge was part of the fun. We raised some seed money, hired a small team and went at it – they in a cool office in Portland’s Pearl district, me staring longingly at said office through video conference on a rolling monitor, like a wistful Max Headroom.

I got to know the problem space, then polished up my wingtips to pitch it a hundred different ways to a hundred different potential users. I flew my cofounder down from Portland to the Bay for marathon days of feedback meetings.

Early signs were positive, partly due to it being a new domain. Plus we were talking to friendly folks who tell you what you want to hear. But as we got further into it, we realized it was going to be a tough road. Developers loved it, but they’re notoriously cheap. The people with money didn’t get it: the product wasn’t solving a deep business pain point yet, just a technical one. It’s possible to build a business around developer needs, but not the business I wanted to run.

After five months of building and pitching, we took stock and decided that it wasn’t going to work. Over the holidays in a hotel room in Ashland, OR, I even put together a plan to merge the company into another startup that was starting to get traction.

I thought the merger was a great plan, but the Portland didn’t share my enthusiasm. This was for a Bay Area company so a merger would make them the remote Max Headroom group.

But we still had some cash in the bank and a lot of ideas. So they were keen to take another swing at the plate. I went along with it.

That kicked off a process of ideation and product iteration. I would come up with ideas, meet with experts in the Bay Area to test those ideas, and then fly up to Portland to further refine the concepts with the team so they could prototype.

Ideation is normally a really fun process: whiteboarding big ideas and open space for how you can change the world. But doing that much of it by yourself and/or remotely sucks. You need the collaboration and whiteboard time. My team was amazing and I loved being up in Portland, but it wasn’t feasible to be there full time given my family and Bay Area-native wife.

After four months of grinding my brain, and meeting with anyone I could for idea feedback and frequent trips to the Rose City (maybe we should have been RoseFrog), we finally honed in on an interesting idea that had legs. And we built out an initial product with 20 different companies trying it out. Problem was: we were running low on money.

While I could have raised more money and kept it going, I didn’t want to run it remotely anymore. The team needed direct, collaborative leadership if it was going to succeed, especially in this “figure it out” stage. I was exhausting myself AND doing a bad job.

It’s one thing if the product ideas are coming out of Portland (like the original idea) and I can focus on selling it. But when it’s on my shoulders to bring new ideas for them to go build, it just didn’t work. If we could have been in the same office, it would have been different.

I thought of finding someone in Portland who could lead the team. We talked to a few CEO folks and even had a great candidate lined up. But the team didn’t want someone else. And the new product ideas were getting further away from the engineers’ passions.

So rather than raise more money and keep going down this uncertain road, we decided to find a good home for the company. Sad for me as I loved the team and felt like I let down them down. But it was the best decision.

My big takeaway: it’s okay to be remote if it’s a known category and everyone knows what to build and sell. But for a new idea, you need to be in the same room. That, and stay away from “Fog” in your name.

While not the ideal outcome, it wasn’t a bad one. And we had a good time, met a ton of amazing people, found a great company in Portland to acquire the team and IP. And we didn’t raise a lot of money so we were able to keep our investors chips on the table (i.e. they got equity in the acquiring company).

And those voices in my head? Much quieter now. More like the “Always Look on the Bright Side of Life” scene.

Most importantly, I learned a lot about myself and what makes me happy. The experience has been the catalyst for a few new passion projects. Stay tuned on that.


Craftwork: How Building a Dollhouse Made me a Better Boss

I’ve always been jealous of people with hobbies. I aspire to have one, but my overly-linear “does it move the ball forward?” filter for life has held me back from an all consuming passion for baseball cards, stamps or old daggers (seriously–Angelina Jolie collects them).

So I was out of my league when I went to a hobby store a few years back on the hunt for a doll house. My daughter was obsessed with doll houses and wanted a “real one” to be her big Christmas gift.

In a split second decision that would haunt me for the next year, I decided to go with the kit instead of the pre-built house as a “fun project to work on together.”

If you haven’t been through this before, a doll house “kit” is something only the guy from A Beautiful Mind could love: a giant box overflowing with thousands of tiny, unidentifiable, easily misplaced pieces of wood, all of which need to be organized, inventoried, sanded, painted (in a specific order), trimmed and varnished, all before you assemble anything.

Sundays over the next year became a mess of paint, glue, obsession, frustration, and trips to the hobby store, where the kind and crafty older women looked at me like a 5-year old who planned to build a car.

Continue reading at

6 Ways ‘Over 40′ Entrepreneurs Can Outpace Younger Rivals

I was 29 when I started my last company. This time I’m 42. Things are different.

Last time, my spare time got filled up with indie rock shows and small batch tequila tastings. This time, it’s more kid’s soccer, kid’s things besides soccer, and the occasional colonoscopy.

My workouts used to include tackle football and full-court hoops. Now I get injured doing pilates.

My big concern back then was a ponderous, “What do I do with my life?” This time, it’s a frantic, “Ack! I’m gonna die. What do I do with my life?”

Starting a company at this age has a lot of stark differences as well. First off, you’re no longer as interesting. At least here in Silicon Valley, where youth reigns. At this point, the VC’s seem to be honing in on 6th graders.

And there’s a reason for that focus on youth: unbridled optimism and energy, “beginner’s mind,” lots of free time and a connection to what’s new and cool.

As a 40-something, you’re supposedly stuck in your ways, not hungry, time-crunched and too focused on why something won’t work rather than why it will.

But my experience has been different. Besides “working smart” as opposed to just “working hard,” there are a lot of advantages I didn’t see coming.


Source: Dave Hersh

10 Questions for Finding Your Next Killer Product


It’s nice to have friends who are brutally honest with you. Say, for example, you abuptly switch from Banana Republic outfits to cowboy boots, a leather bomber jacket, and skull rings. Your friends should be first in line to intervene and let you know that it’s not working.


That kind of honesty is what you want in product feedback at the very early stages of a company. Most of us go out to “friendlies” who, not wanting to offend, tell you what you want to hear about your product (“I could see how comparing my cat’s personaliy to other cats in my area would be quite useful”). But that misdirected kindness will only cause wasted effort over the long run.


Source: Dave Hersh

How to Kill Your Company in Order to Save It

Remember that movie 127 Hours? You know, the true story of Aron Ralston, the climber who had to cut off his arm with a jackknife in order to live? (There can’t be that many movies with that pitch.) As founding CEO at my previous company, I was faced with a significantly-more-creampuffy version of that dilemma back in 2006. We were churning out a profitable $9 million annually in sales and growing at 50 percent a year. Things were peachy. I didn’t know it yet, but I would have to kill off our entire business in order for it to survive.


Source: Dave Hersh

How Strong Company Values Lead to Success

I’ve started posting my blogs on I’ll still do some posts solely on this site, but primarily will be posting there, with teasers to the posts on this site. This is my inaugural post. Hope you enjoy.


“What do you mean “passionate”? Stalin was passionate. Would we hire him?”

It was 10 years ago and I was CEO at my previous company. I had been called out by an employee on one of our core values of only hiring “passionate” people. I fumbled my way through an excuse, but they were right. We had done a great job with a purpose and vision, but the values were vague, trite, and ultimately useless in decision-making or inspiring people. It was like asking the contractor working on your house to “make it more interesting.”

Read More…

Source: Dave Hersh

Stressed to Impress: Don’t Get Derailed by Insecurity

Originally posted on FounderDating


I couldn’t sleep a wink. I was pissed. It was ten years ago. I was the Founding CEO of my last company (Jive Software) and was attending one of the many navel-gazing, Insertbuzzword 2.0 industry conferences.

That day, I talked to a “friend” who was the CEO of a company in a related space. With all the subtlety of a Sicilian stuck in traffic, he let on that his company was going to do in sales that year. And it was twice what we were going to do. I couldn’t believe it. I had worked so hard to crank out our revenue engine. And now we were getting passed. I couldn’t let it go. I decided to get hyper-focused on tripling our sales number for the next year and surpassing that Tool and his company.

Problem was, the whole idea of comparing myself to some adjacent company was ridiculous. Never mind that we had just moved the company from New York to Portland, hired a brand new team and bootstrapped the whole thing. I felt like I was losing a race in my mind, and I obsessed about it. Which was ridiculous. I might as well have been losing sleep over the Bennifer breakup (this was 2004 mind you).

Looking back on that period, it seems obvious: There’s nothing wrong at all with being passionate and focused on the next mountain to climb. The problem for me (and I suspect many first-timers) is that underneath that obsessive focus is intense insecurity that clouds judgment.

dog with frisbee quote


In the early days the misguided motivation was wanting to hire superstars. Then it was big sales numbers. Then it was raising capital from a top firm. More growth, board members, positioning for an acquisition, IPO, blah, blah. Anything impressive.

By themselves, these big goals are not really a problem. But if the outcomes you seek come from an insecure place of wanting to seen and be impressive, you either a) focus on the wrong goals, or b) neglect the work that best supports those desired results for those outcomes themselves.

Some examples of how the insecurity derailed me along the way:

  1. I took shortcuts to the goals. For instance, hiring people to do big deals but who, in my gut, I knew weren’t a cultural fit (and who ultimately blew up).
  2. I made it difficult for employees to confide in me because I had a hard time hearing anything but progress.
  3. I had a hard time enjoying the ride. You always feel like a better life is right around the corner, after you hit your goal, which is never the case. If you don’t hit it, you get deflated and feel like you’ve lost. And if you do, you realize it hasn’t changed things much and you sit in a vacuum while you find something else to take its place.

I see this insecurity in a lot of first-time entrepreneurs who want to prove themselves. Not only in their bragging about investors and customers, but even the way they think about the business. Like putting an “Exit Strategy” slide on a pitch deck. Seems innocuous, but what it often says is that the entrepreneur is unnaturally focusing on the outcome, likely because they equate it with their own worth as an entrepreneur. The reality of “exits” is that opportunities will abound if you build a great company, but focusing on the exit is the tail wagging the elephant. And it’s only going to cause you and your company pain along the way.


This time around as a startup CEO, I’m trying to save myself the pain. Knowing where you’re going and having Big Hairy Audacious Goals is important, but checking your ego and building out systems and processes form the basis for greatness. Focusing on things like:

  1. Doing amazing work every day. “Leaving it on the field”.
  2. Building out the infrastructure to keep your customers thrilled and your employees thriving.
  3. Becoming a true servant leader who is “cloaked” in the needs of the business.
  4. Thinking about process and system goals more than your big company goals, and celebrating those successes along the way.

Thanks to a little help from friends and colleagues back in 2004, I ultimately realized that trying to triple sales to one-up another company was not the move of a stable leader. Over the next few years, we built out a pretty rugged framework for business planning that put the needs of the business and the process goals up front. If we got all the that stuff right, sales would follow.

Usually people who preach to me about being “in the present” and “the journey not the destination” make me want to punch them. Especially non-entrepreneurs. But I’m chilling out in my “over 40” years, and now realize there’s some truth in that overused maxim: fully immersing yourself in the work itself, separating your ego from the equation and focusing on systems and process goals ultimately leads to better outcomes…and a healthier relationship with your company. You know, more like Ben and Jen.

Learning A New Space

A lot of the world’s great entrepreneurs focus their careers on one specific domain, dedicating themselves to building the world’s best [INSERT SECTOR HERE: insurance claims processing software, oatmeal stout, sliding bevel] company.

Not me. I find most businesses fascinating. To me, the process is the product. The act of creating the company gives me the juice. Just being around great people and making it all work. (You can tell because I’ve done software AND software.)

So when my original idea for my current company didn’t stir up interest from potential customers (and hires), I tried not to get my panties in a bunch. My cofounder Erik and I went back to the trough for more ideas. The most important thing was to find a place where we could be the best. Getting too attached to one idea would be a problem.

Being deep in mobile development software, Erik brought a new idea around the large-scale development of mobile apps that was a perfect fit for him given his background. We followed the breadcrumbs on the idea and got a lot of positive responses from folks in the know. Just one catch: unlike my original idea which I understood well, I was a bit out of my league on this technology.

I would have to dig in and learn a new space.

Homer's Quest

How I Approach It

I’ve always been a business leader, not a technologist. My strengths are strategy, leadership, sales, marketing, product positioning, blah, blah, blah. My weak point is engineering depth.

A CEO doesn’t need to be an engineer–and sometimes too much depth can be a problem–but too little understanding will be a train wreck. You need to be very willing to learn and eat your own dogfood, but you also need to hit the right level of knowledge. Think about it like the earth’s makeup:

  1. Crust (the “what”): At this level (common to many salespeople), you get the main concepts, but not why they were created or how they work together. You can speak about the topic but usually need someone else to jump in and help with questions.

  2. Mantle (the “why”): You can speak intelligently about the concepts and design decisions. You understand the entire architecture, but you don’t go deep on the constituent parts. Like owning a house, you should know why you have a roof and how it is constructed to fit with the rest of the house and when it needs replacing, but you don’t need to know what type of flashing was used or the shingling technique.

  3. Core (the “how”): You get how the whole enchilada works together at every level (what, why and how) and can go wherever the conversation goes. People who build the product exist at this level and can answer any question, but there’s a risk of getting too deep (which can hinder decision-making).

As a CEO, I strive to live at the mantle. I like to know how everything fits together and to be able to speak the language, but going too deep in one area will take away from my big picture perspective, thus making it hard to make the best decisions. And it’s probably an indication I’m spending time on the wrong stuff.

How It’s Going So Far

There’s a scene from a classic Simpsons episode where Homer is trying to help get business for a friend’s bowling alley. He does some research. First you see him reading “Advanced Marketing.” Then “Beginning Marketing.” Then he’s looking up “Marketing” in the dictionary. That’s how I felt at first.

But I’ve kept on it. I’ve started coding for iOS and Android, learning Swift (Apple’s new dev language), researching complex computing concepts, taking online classes in data management and structures. And pitching people over and over. It’s like an immersion program for a foreign language – study hard and try it out on real people. You have to risk having egg on your face to make progress.

It can be frustrating. My partner’s knowledge flowed like wine while I was like a bottle of Heinz 57.

But gradually things start to change. It actually starts to become fun. And it starts working. Before you know it, you can chew the fat with the best of them.

So, my advice for CEO’s like me: dig in deeper than your comfort zone. But not so deep you lose perspective. And use middle school geology and food metaphors whenever you need to make a point and/or are on a calorie restriction diet.