How do we disentangle the things that look or feel successful from those that actually make us successful?
March 9, 2016
When Success Doesn’t Feel Successful
Lessons in ignoring your instincts from the founder of EdTech startup Trinket
This piece was originally published on Medium.
I read a book several years ago called The Millionaire Next Door that’s been very influential on my financial outlook. Lately it’s been encouraging me to redefine, as best I can, exactly when I feel like I’m being successful professionally. Let me explain.
One of the Millionaire Next Door’s main insights is that the very things that make you feel wealthy, like buying expensive things, actually make you poorer. Whereas the behaviors that make millionaires, like living in a cheap house or driving an inexpensive car, make us feel poor. Surprisingly, many high flying professionals in expensive suits actually have a very low net worth. Though they own many expensive things, they also have lots of debts that mean that their actual wealth is small. Equally surprisingly, many people of even modest incomes have amassed millions in savings from assiduously spending less than they earn.
While this is all a great lesson (and I recommend you read the book) the real insight I’ve had lately is that a similar phenomenon is at work in the business world. The things that make you feel productive, like clearing out your inbox or meeting with investors, are actually often doing little to get your startup where it needs to be.
Now, though I’ve been noticing this I’m nowhere near being able to resist it fully. Even though I don’t sweat the medium stuff, I feel as falsely productive as the next person when I crank through my inbox. But I have been able to cut out other things, like coffees and random startup events, that let me talk up and feel good about myself and my company but that weren’t doing much to enhance either. By focusing instead on taking big swings at things that really move the needle for us, like the NC IDEA grant, I’ve started being the kind of CEO my team and our users deserve.
Regardless of whether you find my take on this persuasive I do believe that a core competency of a startup founder is to be able to define his or her own success. And a huge part of that is knowing when to ignore false feelings of success. I’m trying to be conscious of this every day and it’s led to several months of best-ever numbers for Trinket even as I’ve essentially gone dark on the local startup scene. This past week I had my first two meetings with prospective investors in about six months. I’m talking that kind of dark.
The balance for you is probably different than it is for me. And, importantly, the value of different activities will change over time. Before you’ve built something people want, you should talk to everyone you possibly can, and I’ve benefitted hugely from sharing my ideas with investors over coffee and with other entrepreneurs at the ExitEvent social and other great events. In fact, at that time, success felt like going into a hole and working on our product but it actually was getting out and talking to people. Now that we have users and a strong product vision, the only people I should be talking to are our users. And, of course, we should be going into a hole and working on our product.
It’s perhaps not fair that exactly the thing that makes you feel productive tends to be the thing holding you back, but that’s part of why startups are hard. It it were easy and natural, everyone would do it and there would be no good ideas left for the rest of us. But the good news is that even without reliable instincts, thoughtfulness and willpower can get the job done.
Here’s hoping that you’re able to succeed, regardless of whether it feels like success. In the meantime, I’ll be over here fighting the good fight against my instincts.