Remembering How We Got Here

I know this guy…when he was about ten…his father lost his job. The father came home one night, just around Christmas, and announced that the company he’d worked for 30 years or so was closing down and he’d be out of a job. This guy always said it was one of the few times he’d ever seen his father cry.

Watching his father struggle over the next few years, bounce from union-provided job to union-provided job, made him feel like he could never ever depend on anyone else to employ him. He knew, he says, from the fact that his father was never the same that he’d never let that happen to him.

That view—that he’d always be responsible for his own employment-dogged him for years.

Then there was the job he had as a teenager. He worked for five years in a locker-repair company. (I know, I know. You never think about it but somebody has to fix all those lockers in school.) Anyway, it was a great summer job. He’d work from early in the morning until mid-afternoon and still have time to go out with his friends at night.

Even better, he worked for this older man who, it seemed, was completely unlike his father—especially when his father was unemployed and sitting around the house. The older man could fix anything and taught the guy how to use his hands. And in doing so, the guy always says, he learned that—if nothing else, he knew how to swing a hammer. He’d always be able to work.

College came and with it a series of survival jobs. Each took him further and further away from his childhood and deeper into his manhood. One year he won a scholarship and a summer job from a publishing company and he turned that summer job into a permanent part-time position until he finished up school when he was hired fulltime.

Later, after a few years at the publishing company, the guy’s father advised him against taking a job that would require him to move. It was promotion out of his current job—a place he’d been working for a few years—and his father cautioned that the “higher up the pole the monkey climbs, the more his ass shows.” He followed his father’s advice but he stewed on it, it gnawed at him.

Later, when he was about eight or nine years into what had become a career at that company, he remembered the advice, and more important, remembered the regret. And so when an opportunity to be promoted, to take a risk, to take a job off the successful track he was on, he decided to go for it.

It helped, in a way, that when he went to his then boss to announce he was taking the internal, lateral promotion within the company, the boss went ape-shit; told him he was an idiot, that he’d never amount to anything, and he’d be stuck in the dead-end corporate job forever. And when the guy just stared at his boss and said nothing, the boss said:

“I know what you’re thinking…you’re thinking you’re going to take this job and prove me wrong.”

The guy stood up, calmly said, “That’s exactly right,” and walked out into the rest of his life.

That guy was me.

After I left that job—as Editor of InformationWeek—I ended up, after a stop, working with a group that started TechWeb, one of the earliest entities on the Web to accept advertising. And after that, I left the company and started a ten-year career as a venture capitalist.

There are dozens of events that shape our careers, our lives. There are the little conversations at the end of the day, over a cup of coffee, that reframe everything.  There are the daily mantras we grow up with that shape our values and our sense of the right thing to do in life. And there are the large events, like when my father lost his job, that cause us to take on a new point of view, a monster if you will. In my case, that view has sometimes cost me but more often than not caused me to push ahead, to try different things, to explore, to take risks. In a way, I wouldn’t be the man I am today had I not watched my father struggle through his years of un- and underemployment and had it not been capped by that fearful advice he’d given. For good or for ill, and in full-blown rebellion against my father, I’ve never been afraid to let more of my ass show.

Today, as a coach, I consider myself one of the luckiest people alive. I get to hear peoples’ stories. I get to help people merely by listening deeply and holding onto their stories while they do their work. And among all the things I find so remarkable are the ways in which our lives are shaped by these conversations from our pasts.

In a book I often use in my work-especially with men–psychologist Samuel Osherson explains the impact of these real and imagined conversations on our current lives:

It’s not true…that your father comes to you only once and forever; you meet him again and again in different guises through your whole life. We relive with our mentors our ambivalence over our fathers’ messages as to what it means to be a man. Many men learn from their fathers that to be in the work world means to suffer, indeed that manhood itself is a kind of dreadful obligation. Finding Our Fathers: How Man’s Life is Shaped by His Relationship with His Father

It helps to understand the stories of our lives. It helps to see clearly the ways in which a word or two changed everything. Seeing the patterns that ripple out from those tossed stones of events, conversations, and interactions allows us—if nothing else—to see even more clearly how we became who we are. As I often say with my clients, a good first step to figuring out where you want to go is remembering how you got here.

  • Tereza

    Profound post, Jerry. Thank you.

    There’s a lot of change in the air right now. Maybe it’s spring….trying to decide which luggage we’re taking with us and which we’re not, into this next cycle. Which of them propel us forward, and which ones hold us back.


    Back to doing my taxes. They’re definitely holding me back.

    • jerrycolonna

      Some things never change…death, taxes and the luggage from the past.

      • Tereza

        Ain’t that the truth though. Sheesh.

        All I can say is, if my dad were alive, I’d be working at IBM right now. His dream, not mine.

        No doubt we all have very personal stories on this one.

        Bizarrely, twice in the last week I thought, “what’s Jerry saying?” and you’d just posted something minutes before.

        So — if I ever manage to get funding, I’ll make sure to tell them I need a good coach. Someone with the initials ‘JC’. :-)

  • paulhart

    Oh man, I have to laugh at myself, I’ve attempted to write something twice now and closed my self [sic] down both times. I’ll leave this comment as a marker to myself though, it has slightly more permanence than me just closing the window.

    • jerrycolonna

      Glad you could do both…laugh at yourself AND leave the comment.

  • Peter Cranstone


    That one word defines how I got here. Along the way (my life) people have popped in regularly to advise me that I won’t make it. In essence they say just say “No”. I remember two instances – one where I was working on the data compression problem where the inventor died. I spoke to one of the inventors of the Gzip algorithm. A brilliant individual himself he advised me that I was wasting my time. In return I replied it was my time to waste. While the product never succeeded I went on with my current partner to invent Mod_gzip (we made it do in real time with a web server what the inventor of the algorithm hadn’t). A No turned into a “Yes I can and I did”.

    My other famous No was from a very prominent venture capitalist who works at a very large Palo Alto fund. I’ve never forgotten that meeting to this day. He chewed me up and spat me out in about 5 minutes. But then he said something that I’ve never forgotten – I think there might be something here, you have the remaining 55 minutes of your meeting to get it out. I couldn’t because the idea was half baked and I didn’t have the answers.

    I left and went back to work – 6 months later he wouldn’t have done that again, but by then it was too late. But that No turned into the current Yes. My current startup has already had several people say it will never work – but it does and I believe in time they will see that it’s an elegant solution to a very complex problem.

    So what got me here? No.

    You have to have No’s to see how far you’re willing to go to solve whatever problem you’re working on. Along the way I’ve met some of the best “No’ers” in the business. Every meeting starts out with a No – just like it did with mod_gzip. And then I ask them if they use the product that everyone said would never work or get installed and they all say – it’s awesome, we’ve never turned it off”.

    Don’t let the No’s stand in your way to “Getting to Here”.

    • jerrycolonna

      Peter you’re doing it again: writing comments that are better than the posts. Yeesh.
      Seriously good point about confronting the No’s…I’d even suggest that I had done exactly as you suggest when dealing with both my father’s “advice” and the attack by my boss. I turned the implicit No into a yes.

      • Peter Cranstone

        Thank you – but it was you who first inspired me, and then allowed me the freedom to post without judgement. You’ve created and are fostering an environment that allows people who hear “No” everyday to talk out loud without fear of a No. I can’t tell you enough of how wonderful that is.

        • jerrycolonna

          I love this. Thank you.

  • Shane Taylor


    I follow approximately 70 blogs that I am sure many other entrepreneurs follow as well. I don’t really ever comment on posts (which is something I need to improve on). However, your posts are somehow different (at least to me) and I feel the need to mention that. I feel like we have a common drive that is fueled by similar reasons. Regardless, if that is the case or not, I wanted to let you know that your posts are very inspiring to me. Just like certain music and images trigger emotional response, your posts motivate me very strongly. I figured I should, at a minimum, say thank you.

    • jerrycolonna

      Thanks for the compliment Shane. It means a lot to me. I really enjoying making a difference in peoples’ lives and to hear that I touch you, motivate you, trigger thoughts and feelings…well that’s a gift to me.

  • Bags

    Yet another inspiring post, Jerry. I just spent 4 days away from little ole’ Utah in New York City in interviews and networking meetings with some pretty amazing people. I’m so tempted to leave permanently. The allure of the big city, small startups and great minds is almost overwhelming… but it goes against all of the conservative life lessons my parents have fed me since my youth.

    Get a good job. Work your way to the top. Live frugally. Stay close to your family. Retire at 65. It sounds nice… but I don’t think it’s me. Making the leap will be a direct assault on my Father’s way of life. It’s a big risk and a hard decision to make. Your experience is encouraging. Thanks yet again!

    • jerrycolonna

      You’re welcome Bags. Glad you got to enjoy NY

  • davearkoosh


    You write a great a blog.

    One of the most nagging questions I’ve faced in my short career so far is what advice to consider and what to brush off. The biggest rub here is wanting to please everyone by taking their advice to heart. It leads not only to taking too much bad advice, but to total decision paralysis. I think what I’m learning is that everyone can and will find a reason to say “No,” but when someone skips the nay-saying and wants to discuss the upsides is when I need to start listening. I’ve found that when advice is contributive as opposed to negative or “can’t do,” it’s generally coming from someone worth listening to. Bottom line: Telling people where they can’t go will never get them there.

    • Tereza

      Hey Dave,

      Your question was directed at Jerry and no doubt he’ll have something more illuminating to say.

      But FWIW i have 2c to pitch in here. Last summer I read Keith Ferrazzi’s “Who’s Got your Back” and it made a really huge difference for me. He says create your own personal informal “board of advisors”, people who have successfully achieved what you want to achieve and also that care about you. Maybe 2-4 people. Try to select ones who are strong in various areas of your own vulnerability, or key areas you want/need to grow. Select them judiciously. You need to genuinely like each other.

      Try to meet with each one at least quarterly, and phone them as you need. They should know very well what you want to achieve and want to help you get there. But also you need to be clear that if they see you doing something patently wrong, they should tell you.

      I picked a bunch of serial entrepreneurs. They are about Yes. This helped me break through a wall. Before, I was focusing on VCs, and they are predominantly in the business of saying No all day long. It was a buzzkill. Oh, and incidentally, a lot of those serial entrepreneurs do angel investing. So you may be unwittingly convincing them to put in some seed capital, when they observe over time how amazing you are.

      So what your “board’ tells you should carry more weight than your average joe or the naysayers.

      No doubt Coach Colonna will have something very wise to say. But that’s my peer-to-peer from-the-trenches report.

      • davearkoosh


        That sounds like a great model, and I will take a look at “Who’s Got Your Back.” I like the idea of having honest advisors, but also ones who can help you break through walls instead of merely casting knee-jerk judgment on a plan, which is usually in the negative.

        Thanks for the constructive feedback!

        • Tereza

          Hey Dave if you want i can mail you my copy. I don’t need it anymore. if you email me at tnemessanyi (at) gmail (dot) com with your address, i’ll send it to you. Feel free to keep it or pass it on from there. trying to reduce my # of objects.

      • Peter Cranstone

        Hi Dave,

        Just echoing what Tereza has to say. Advice is only as “good as the paper it’s written on”. Some of the best advice that I’ve ever had has always had a certain quality about it – it’s non judgmental and is lacking in agenda.

        I never forget my grandfather saying to me – “Peter my boy, wherever there’s a tip there’s a tap”. Meaning someone always has advice on something. The key is to figure out the “tap” because if you don’t experience will step in and teach you a wonderful lesson.

        One other lesson I learned was to view “the problem” like a large table. No one person (except the man upstairs) knows all the answers. Look for advisors that bring illumination to various parts of the table. Soon it will be well lit and you will be able to determine whether or not you should proceed. It’s always up to you to determine the validity of the “No”.

        • Tereza

          I love that table metaphor, Pete! Own the table, Dave — and decide who sits at it.

          And Pete, you sure do come out with one great comment after another. Wowzers.

        • davearkoosh

          The table metaphor is great! Now just to illuminate the table and not occupy the seats with those casting shadows of pessimism.

          Also, it seems to me that the “tap” is often the advice-giver’s own insecurity. The advice-seeker’s idea will never make it because the advice-giver isn’t on board or it wasn’t their brainchild to begin with. Sometimes it’s merely that insecurity or perhaps an artificial barrier to entry protecting their turf from new players.

          Thanks, Pete!

          • Peter Cranstone

            The table is a powerful metaphor. In the past I’m managed to surround it with all the wrong types of people. What I’ve learned (the monster in my head) is that I never believed enough in myself and was using/relying on others to fill my insecurity needs. (It’s not their job).

            The old adage is true – start with the end in mind. Then work backwards to fulfill the objective. You will meet people, they will have agendas (everyone does) – the “tip” is to find the agenda that most closely aligns (key word) with your vision.

            These people will help you succeed.

            When I started my latest venture I wrote down what I wanted to achieve. I still have that document – the first two items were the same… to help my partners be successful and to solve a significant customer problem. I’ve never altered my objectives, and as time moves forward I’m now meeting people who are really helping me to succeed.

            It all started with the definition of the table – after that comes a lot of patience and belief in that your doing the right thing.


          • Peter Cranstone

            I meant to say – the first two items are …. not the first two items are the same.

  • jchewitt

    Thanks for your honesty and courage, Jerry.

    I spent most of my morning thinking about it. The hardest thing for me in processing my relationship with my father has been separating the positive aspects from the negative ones. It was easiest for me to reject everything – to disown the part of me that he impacted. But that was immature, even if it was appropriate at the time.

    • jerrycolonna

      I know that struggle jchewitt. Don’t be so hard on yourself though. Seeing things as they are, accepting all the aspects of our legacy, is a process and takes time.

  • Craig Plunkett

    Thanks for the story. I also had a formative experience like that. When I was 15, my Dad came home from work and said, I have good news, and bad news. The bad news was that he lost his job at a small refrigeration firm. The good news was that he found me a car for $100 that we split 50/50. It was a 69 Mustang that didn’t run because somebody put out a fire in the intake manifold by throwing sand down the carburetor’s throat. Together we got the car running, and my father started his own HVAC and energy management business.

    He was able to make enough to support a family of 5 kids into reasonably well-adjusted adulthood.
    33 years later, he is close to the end of his business run and has been my role model for perseverance and self-reliance. In my career I have gone from technician, to entrepreneur, and on to corporate executive with more in store. There are events with and components of our fathers ( and mothers ) that make us who we are. Sometimes they serve us, and other times, undermine us.

    Without being self-aware you will be at sea, rudderless.

    • jerrycolonna

      And thanks for your story plunkman. You’ve added greatly to the dialog.

  • Dave Manningsmith

    I tell people that there’s only one piece of advice I feel comfortable giving anyone: only follow advice that resonates with you. Everyone has advice. They’ve learned things from their experience that they want to share to help others. That pretty much guarantees that if you seek enough advice, you’ll hear diametrically opposing views, often leaving you with more data and less direction. Most advice is good advice, in the right context. So only take advice that seems right to you, that seems like a natural extension of advice you would give yourself. The other advice might be great. Maybe later, you’ll wish you’d followed it sooner. Don’t second guess yourself. If advice doesn’t resonate with you now, you’re likely to follow it badly. You’re on a journey. Small shortcuts are useful. Giant leaps off your current path and onto some other path aren’t shortcuts so much as teleportation, leaving you disoriented, unequipped with the experience of getting there through ways you understand.
    Hope this makes sense and adds value.

    • jerrycolonna

      It does both Dave. Thanks.

    • Tereza

      My darling husband, if he were participating in this conversation,
      would step in at this juncture and add the following:

      “Opinions are like asshole. Everyone has one, and they all stink.”

      • jerrycolonna

        The thing about advice is that it’s more often about the giver than the receiver. It took me years (I’m a slow learner) to internalize this but it’s something I see in my work over and over. My father’s fears about being “climbing the pole” were about his fears about failing, being hurt. Of course, at the time, I took it as a challenge to me.

        Something I often say to clients is to be wary of any line that begins “You know what you should do?” More often than not what the well-intentioned speaker is really saying is “What I would do if I were in your situation is…”
        Which can be helpful data, but is often irrelevant.

        • Tereza

          Yeah, i’m sure that 95%-99% of the advice I (liberally) dole out is about ‘moi’ as well. got to be careful.

          When I was about 16 I made fun of an English mistake my dad made (that was really hysterically funny). He was apoplectic. He screamed, “The day YOU speak seven languages, THEN you can correct my English!”

          Click. An obsession took root. Decent goal, in moderation, but jeepers, how impractical. Eventually, thankfully, I abandoned it for greener pastures.

        • Tereza

          Just reflecting here….another element, beyond the emotional, is the nuts-and-bolts financial situation the advice-giver. Can drastically color the advice they (we? I?) dole out. For example, and this has happened to me, a gazillionaire advisor may be brilliant and ‘been there done that’, but may be very far from the bootstrapping mindset. So if the advice is about how to spend your (meager) money, you really do have to take what they say with a grain of salt. So one thing I often do tell people younger than me (and perhaps I am projecting), is feel free to own your tight financial situation. There is absolutely no shame in it and in fact they can be totally proud of making tough choices they believe in.

          But back to the topic…advice seeking, when too many people are asked, crosses the line into market research. And if you must for whatever reason tread into market research territory, then frankly your best served treating it that way, with some degree of dispassion. For example, a moderately representative sample, very carefully crafted questions, data analysis and the like. I have conducted a huge amount of market research (quant and qualitative) for clients. If there’s one takeaway, it’s that each subject you ask is simply a data point. Only do as much and as rigorous research as you feel comfortable with, and own the analysis/interpretation.

          There will always be conflicting information. Your interpretation, and what you choose do with it, is your special sauce.

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  • Barrett

    One of the best posts I have read. There are many monsters in the head. A daily battle

    • jerrycolonna

      Thanks Barrett. I agree…many, many monsters.

  • casinoman88

    Another great post. Thank you.