What advice would Pittsburgh tech leaders give their 2009 selves? Set work boundaries and invest early

As the saying goes, hindsight is 20/20.

But in 2024, Technical.ly is celebrating 15 years in business, so we’ve been looking back and reflecting on what we’ve learned from our years covering tech. We’ve also caught a glimpse at the past lives of some of the region’s esteemed technologists and execs.

To keep the momentum going, we asked a few more: What would you say if given the chance to give the 2009 version of you advice?

For some of Pittsburgh’s finest, the answer was to set boundaries between your job and the rest of your life. For others, the advice was simply to be more confident.

Then, just for fun, we also asked about their favorite 2009 or 2024 tech tools. Here are their full responses:

KEF Robotics COO Olga Pogoda

I would tell myself to be more confident and not be so afraid. To listen more and work more efficiently.

• Favorite 2009 product: My favorite device at the time was an iPod Shuffle!

Dashcam for your Bike founder Armin Samii

Companies will try to make you feel like family so that you work long hours for them. Don’t give in. Your nights and weekends are yours. Your vacation is yours. Turn off Slack notifications. If you want to work long hours, you deserve equity commensurate with the hours you put in. If you want to work harder, work on a side project — it will pay more dividends in the long run.

• Favorite 2024 product: The dashcam.bike app makes me feel less helpless when riding my bicycle. The everyday hazards I encounter are no longer isolated frustrations, but help my city build a picture of where bicyclists are in danger, and where better bicycling infrastructure is needed.

Pittsburgh Technology Council SVP for Operations and Government Affairs Brian Kennedy

When speaking publicly, always announce that my opinions are mine alone and might not reflect the opinions of my future or past selves. It’s OK to evolve!

• Favorite 2009 tech product: Nikon D50

Code & Supply Managing Director Colin Dean

Put your money where your mouth is, as literally as that can be taken without literally eating cotton bills. Retirement and other investments shouldn’t wait; even small amounts benefit from compound interest.

• Favorite 2009 tech product: My G1 Android (T-Mobile G1/HTC Dream) was less than a year old at the time. It’s amazing what Android has become in that time, despite me never actually having written an Android app — something that was always on my to-do list.

How about you? What would you tell your 2009 self? Let us know at pittburgh@technical.ly.

Atiya Irvin-Mitchell is a 2022-2024 corps member for Report for America, an initiative of The Groundtruth Project that pairs young journalists with local newsrooms. This position is supported by the Heinz Endowments.