When I left my job at the NSA to work on Collage.com, people thought I was crazy – not for starting a company, but for pursuing photo products when security was such a hot area.
This reaction I got is precisely why it was a good idea. Top engineers wanted nothing to do with photo products, so everyone in the industry had terrible software.
With zero investment, we bootstrapped to $86m revenue and sold to private equity in 2021.
Did I love photo products? Probably not. I certainly had some aptitude and interest in photography, but I wouldn’t say it was my life’s work.
Instead, I was drawn in by opportunity.
I knew enough about software to build a cloud-based service for rendering large images (back in 2008), and enough about design to make a decent UI for building collages.
Shutterfly’s UI was so bad that it felt like an obligation to offer something better.
The economics were also attractive, with 60% gross margins, no up-front-capital, and not having to pay bills for 30-60 days.
Then came the daily deals. We rode this wave during the brief time it was profitable, growing from $100k to $14m revenue between 2011 and 2014.
Finally, after growing to $50m revenue in 2019, COVID gave us a huge surge in 2020. Revenue went up to $86m, and net profit increased 8x. We sold to private equity in 2021.
If I had prioritized my passion (computer science research), I’d have missed all the opportunities to learn, grow, and step outside my comfort zone at a fast-paced start-up. I also wouldn’t have the built relationships, skills, and financial resources that allowed me to do whatever I wanted next.
Doing what you love instead of following the best opportunity is like driving directly to your destination rather than taking the highway. Good opportunities take you anywhere you ultimately want to go much faster, especially earlier in your career.
Another hazard of doing what you love is that love can fade over time.
It’s always exciting to explore a new area and encounter fresh ideas on a daily basis. During this honeymoon period, positive emotions flourish.
Once you’ve walked every path, however, things start to get dull. You become aware of the roadblocks that hinder progress, and realize that other people have already thought of all your good ideas.
If love was your main motivation and that love goes away, you have nothing left.
I have worked with people in the past who started out with a lot of excitement, but gradually lost interest after about 3-6 months. True success takes years of dedication, and relying on love alone probably won’t be enough.
Regardless of what you pursue, success takes grunt work that you will not enjoy. You may have to deal with office politics, clean toilets, or do odd jobs to make ends meet in order to achieve your goals.
The problem is, if you’re only in it for love, then you might have a hard time finding motivation for the unglamorous but essential tasks.
I have had negative experiences working with passion-driven people where they didn’t want to do tasks they found tedious like writing software tests, even though those tasks were critical for achieving long-term outcomes.
When you love something, you have an emotional attachment that goes beyond the desire to reach an outcome and may transcend practicality.
In a real-world organization, resource constraints force you to compromise. If you are too emotionally attached to your work, you may have a hard time doing what is necessary to succeed.
I have seen this take many forms, from reluctance to raise prices on customers because you feel like one of them, to not wanting to ship software that’s lower “good enough” quality or copied from a hated competitor.
Emotions can be a powerful asset, but sometimes making the right decision requires a level of detachment that is hard when you’re doing something you love.
It is important to find satisfaction in your work, which is essential to have motivation.
However, it is also important to work toward a goal and reach that goal so that you can move on to the next task.
When motivation comes from loving what you’re doing rather than being done with it, it’s easy to get carried away and spend way more time than necessary.
I have worked with software engineers who struggle to complete tasks on time because they simply enjoy the process too much and over-perfect their work. Those who see coding more as a means to an end are more effective engineers.
People who choose the path that they’re on out of love have a strong desire to stay on that path. While perseverance is admirable, sometimes you need to quit.
After we sold Collage.com and merged with ShootProof, which sells gallery software to professional photographers, things went south quickly. I’ll spare you the details, but it was a bad environment and a lot of people left within a few months, including myself.
However, a lot of people stuck around because they loved photography, were photographers themselves, and cared deeply about customers.
These people put up with poor treatment out of passion for photography, which made the problem worse because managers took advantage of the fact that they’d stay regardless of the circumstances.
Being disconnected enough to walk away from your work is important to avoid getting stuck in a place that no longer offers good opportunities.
Unless you’re a rare person whose talent and passion align perfectly, following your passion instead of your talent takes a toll on society.
If you are a brilliant accountant but pursue medicine because you like to help people, then another less talented person (who might be better at medicine) will have to do the accounting anyway, making everyone else pay for your choice.
Working on something you love is rewarding, but you may not learn much.
When I look back at all the things I had to do at Collage.com, the ones that most made me a better person were those where I had to overcome tremendous anxiety and difficulty.
I had no initial passion for hiring, and nobody enjoys having to fire underperforming employees. But, in seeing the negative impact that bad hiring decisions had on my friends and colleagues, I found motivation to overcome my fears and get a lot better at building cohesive, high-performing teams.
If you only focus on things you love, life and all of its rewarding challenges will pass you by.
After leaving Collage.com, I was lucky enough to have the freedom to do what I wanted next. This was great, but it also made the decision difficult.
I am actually very passionate about education. Looking back at my own experience, I see a lot of slow growth and missed opportunities. Working with new graduates, I saw them struggling in the same ways due to gaps in their education.
I firmly believe that society could be 100x better if education enabled everyone to reach their full potential. Now is also the time for disruption due to worldwide internet connectivity.
And yet, actually starting a school or education platform is fraught with problems.
I don’t know that much about education since I’ve spent my career building software. While it’s easy to see problems with the education system, I probably take for granted a lot of the things that it does well, all of which I’d have to learn.
Educators also have to handle the challenges of working kids and parents – dealing with harassment and bullying, talking to parents who have unreasonable expectations, etc.
Then there’s the matter of financing. Students most in need of education have no money. I have no experience with non-profit fundraising, but I imagine it is much harder than raising venture capital, which is already a challenge.
On the other hand, taking an objective look at the intersection of my skills, experience, and market opportunities clearly pointed in one direction: software engineering analytics.
I have been building software professionally for 20 years and managing engineers for 10. I have already gone through the Dunning-Kruger cycle of initial overconfidence followed by disillusionment and then developing expertise.
Despite enjoying teaching, I am probably a lot better at building software, even if it is less new and exciting for me at this point.
On the market side, there’s enough interest in engineering analytics that several companies have raised venture capital. At the same time, I know that competition is weak because I managed a successful engineering team and saw how inadequate their products were in a real environment.
While engineering analytics won’t directly give my children a head start in life like education would, I have seen the pain that bad management inflicts on people. If I can help millions of software engineers feel less stress and have more time to spend with their children, then that is probably the best thing I can do for the world, and the right decision for me.