Are you learning from your younger self?
There’s a common question they ask at fireside chats and in interviews. “What advice would you give yourself at age ‘X’ if you could go back in time?” But, I think a better way to frame that question is, “What could you learn from your age ‘X’ self if they came forward in time?”
I was thinking about this over the weekend. I’m not sure if it will help anyone or if it’s a common framework of thought and I’m just really late to the party. Either way, I thought it would be useful to at least write about.
“Your younger self was going through specific problems, and suffering through specific failures.”
Whenever someone talks about advice they would give their younger self, it’s usually some macro-focused thought. Like, be more patient. Or, spend more time with family. These are all good things, and solid advice. But flipping it, and reversing the question, allows us to get more specific — more into the weeds. Your younger self was going through specific problems, and suffering through specific failures.
Fundamentally, I think we learn more from our failures than our successes. So when I originally had the thought, my brain immediately went to — what could I learn from a “young me” about some of my all-time failures?
Now, I had already racked my brain when these failures happened to see what I could learn from them and move forward. But as I sat reminiscing I realized there were more lessons in the failures than I originally thought. This then led me to a couple conclusions. It’s hard to learn lessons from a failure immediately after the fact. And I have a lot to be grateful for.
We don’t know what we don’t know.
Immediately following a failure, as we’re accepting our ‘L’ and brushing ourselves off, we try to analyze why we just failed. We usually come up with a few answers that we think make sense, draw parallels to other things that have happened before, and come to a conclusion on what we’re willing to try again, and what we’ll never do again for whatever reason (usually because we think it won’t work). But what context are we using to analyze these alternatives? What new perspective have we gained? We literally just failed at this thing. Are we so much smarter now — a week out — than we were when we were falling on our face? Maybe a little bit, from sheer experience, but not that much if we’re being honest. And there’s a very good chance that whatever little analysis we’ve done is completely wrong.
It’s when we’ve gone and learned a lot more, done a lot more, and have a ton more knowledge in our arsenal that we can look back and really dissect our failures properly. With a new perspective, we realize where we were completely wrong and what we should never have done in the first place. Or it finally clicks — the one thing we could have done right that would have changed everything.
Also, the exercise gives us an opportunity to look back at how much we’ve learned since that failure. How much more experience we have and how far we’ve come. It gives us an opportunity to be grateful.
My first real business failure.
What really kick-started this thought process was thinking about one of my earliest failures. Before I moved to New York, I co-founded an event business with a few friends in Jamaica. We launched about 3 independent event concepts and hosted a few smaller event series. It wasn’t a very big project, but it was my first attempt at starting and running a real business. I was managing a P&L, running sales, creating partnership opportunities and leading our marketing efforts.
We had built up the confidence to start the business because we hosted a few successful events when we were in school. Some after-school socials, Kiwanis club events, and just generally hustling at everything to make money. We figured, we’re older now, we’ve done it before, we should be able to easily “draw a crowd” (fill an event). Boy were we wrong.
“I cried as we packed up that night.”
The first event we did was a disaster. Before we even launched we had trouble negotiating the deal for the venue, then we had trouble negotiating the right deal with our liquor provider to get alcohol on consignment, and we struggled to find sponsors. The nail in the coffin was that on the night of the event, after all the struggling and fighting to make it happen, the event was empty. Only a handful of people showed up, and we had nothing to show for all the planning and work we did. It was a really cool concept too. I cried as we packed up that night.
It didn’t take long for us to dust ourselves off, though. After about a week, we got over it and started planning another event for the summer — 6 months away at the time. We were determined to learn from our mistakes. We partnered with another group, mastered our marketing strategy, got some sponsorship deals, got better at surprise and delight, and we were on our way. That’s when I learned the true power of Facebook. It was 2007/2008 and Facebook’s organic reach was through the roof. People were just getting off of MySpace and flocking to it in droves, and everything we put up — everyone would see. It was a great time.
The next event was much more of a success. We didn’t make a lot of money and still struggled with A LOT. But not making a lot of money sure beat losing a shit ton of it (at least it was a lot to us at the time). We learned enough from our first event to get better, but there was still so much we didn’t know. We were just throwing sh*t at the wall and whatever stuck we ran with it.
Thinking back on it now, with more knowledge and a better perspective, I can point out some of the exact reasons we failed.
Timing.
Our second event may or may not have been better executed, but it was certainly at a better time of year. Back then we weren’t thinking about it like this, we were just getting up and going again, but 6 months later in the summer was a much better time for an event. People were in a more relaxed mood, and we weren’t competing with more established event brands like Bacchanal during Jamaica’s carnival season. As a new venture, we didn’t have the resources or knowledge to compete with more established brands. We didn’t have a clear, identifiable differentiator. Nor were we operating with any customer insights that would allow us to make better decisions. (Our second go at it we just got lucky on timing)
Product/market fit.
This is something I wouldn’t learn or understand until years later when I started working with start-ups in NYC. We were creating these event concepts for a more mature audience, with mature DJs, and mature packages, building what we thought was the ideal product. But not the product that suited the market we were operating in. Because we didn’t have a lot of money for traditional marketing spend, a lot of what we did was built on top of these new digital channels like Facebook. And if you know anything about Facebook back then, it hadn’t aged up yet. So for our first event, we promoted this super mature event for “lovers” on Valentine's day, while our audience was essentially college kids. We did find a better product/market fit our second and third go-round, but only by accident, and we didn’t even do it right. If we knew exactly what we were looking for we would have knocked it out of the park.
Scaled too big, too fast.
This one is pretty self-explanatory and obvious now. But we went from what was essentially these small social type events, right into major productions. And we obviously didn’t have the infrastructure to manage something like that. We were getting way too big for our boots (Big up Stormzy).
Neglected Sales
After spending years growing up under my father’s roof — a natural born salesman — I feel ashamed to say this. With all the planning, strategic decision making, creative and digital execution we did — we neglected the most important thing. Sales. Our lack of appreciation for sales was our single biggest failure. We spent time on everything else, and little time on actually selling tickets. I guess we thought our product would be so great that people would just come chasing after us to get it. We depended heavily on friendship networks that didn’t materialize anything.
Even our relatively successful events later on still lacked a proper sales channel. It’s a testament to every other piece of our process improving why we were able to see any fruit at all. That, and more people started joining Facebook.
“You can’t fix a problem if you have no context to know that it’s a problem in the first place.”
The point I’m trying to make is that it wasn’t until years later that I was able to identify a lot of the mistakes I made. Maybe at the time, I was too young to understand. But really I think I just didn’t know. You can’t fix a problem if you have no context to know that it’s a problem in the first place. I could have spent months trying to analyze what happened, trying to see where we went wrong. But without the proper knowledge and the additional years of experience to provide the much-needed perspective, it would be pointless.
Failure is inevitable if you’re pushing and shoving and trying new things. But find out what you need to learn from the failure and start looking at different frameworks for your thinking to improve your perspective. Go out and continue to gain more experience and realize it will take time for you to truly learn from it.
More importantly for right now, think back on some of your all-time failures. What have you learned since then, and what can the failures of your younger self teach you today? The things I take for granted that I know now, framed in the perspective of my younger self, really helped me regain some focus in a weird way. I personally can’t wait for 10 years from now, when all my failures of today will be some of the best lessons of my life.
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This post was originally posted to Linkedin. I hope you liked this. If you did, please share it, drop a “like”, and leave a comment. I’d love to hear from you and get your thoughts on this. This was literally just a brain dump, so if you disagree or have a different point of view I want to hear it. Help me improve my perspective.
MF
