I am not a tech head, as you may well know. However, there are some items of equipment that I didn't upgrade that have ended up holding my commercial photography career back.
I have never been one for buying things. I actually own two pairs of jeans, 10 black t shirts, 5 white shirts and enough pairs of pants and socks to last me 7 days. Besides that I own a small car, push bike, mobile phone, and a coffee machine. I seem to have taken this approach to life to my photography too. I am a big fan of having fewer items and making them last until they can't be repaired anymore. Far from a minimalist or any eco push, I just find having fewer items to be less stressful. However, this approach has held my career back several times, and continues to even now.
Some upgrades don't really help that much. A new camera body, new triggers, or perhaps a new camera bag probably won't help you out all that much. However, as I discuss in this video, there are some items of photographic equipment and computer equipment that can have such a profound impact on your ability to progress as a professional photographer that I have been a fool not to upgrade them sooner.
What do you wish you had upgraded sooner?