What were you doing the last time you felt successful that you’re not doing now? My girlfriend asked me this loaded question while we were casually discussing life and the rut it seems everyone we know is in. It’s true. All the folks I spoke to last week were frustrated and questioning what’s going to happen next for them. I’m hearing from so many lifetime entrepreneurs that are heading back into corporate roles – at least in part, they tell me, because they never felt successful. 

A few of the answers to this big question for me came up quickly. I missed being a creator without a set business model and a plan. I spent most of the early days at Three Ears Media creating downloads, videos, and blogs simply because I thought the topic was interesting. I didn’t have click-tracking data to make me focus on one topic. As I’ve spent more time on understanding what makes me feel successful, I know now what I miss most of all – and it’s not the autonomy of the decision. It’s the advice I give every entrepreneur when they’re starting out: connect. 

In the first year of Three Ears Media when I had no idea what success would look like, I made it a point to contact three people a week. When someone asked how they could help me, I’d ask them to introduce me to someone. Then, every day I tried to contact three more people who might have advice or ideas for me. Reflecting back on this business, those people fundamentally altered the path I was on. I still reference some of their advice today.

One offered advice about my time. She flat out told me to stop doing things that are not my strength. She saved this business. I would have quit a long time ago if managing contracts was on my to-do list. Another told me to find a niche. Clearly, that stuck. I focused in on job postings and I’m so glad I did. The other one was to always do my best, and then let it go. That person saved me a lot of heartache with clients that would never be satisfied. 

At some point in my journey, I didn’t ask for introductions anymore. I stopped making those calls. I didn’t notice the shift at first. I was just going to ChatGPT and Google with the questions I used to ask people. It was faster; at least that’s what I told myself. I assumed I could figure it out with the digital intel.

However, as much as the technology was faster, it just provided a list of suggestions without the part that made people’s insight so valuable: the context. The part where they told me why it mattered or how it worked for them. People who have been there before can tell you stuff the blogs trying to sell that product or those services would never. The stuff AI can’t conjure up, because most people don’t post their business advice online. They think it has already been done. Damn their imposter syndrome. 

So, as we plan for a future where new technologies transform the way we work and success sometimes feels far away, my advice is that you invest in connecting more. Don’t just bet on your hard work to add up to a feeling you crave. Entrepreneurship isn’t a reward system. Every sacrifice you make won’t add up to feeling any different if you don’t invest time in finding different opinions. Don’t hurry toward figuring things out to feel successful instead of finding out why or how. This rush toward answers ultimately leads to negative consequences – in the tech and talent. It creates a world where it’s pretty easy to tell yourself that you’re just not successful. 

I know. I’ve been there. Beating myself up over a digit or decimal point. Telling myself I just didn’t work hard enough and all the other lies we say to make us feel like work is all just a controllable formula we got wrong. Surely that’s not the formula for feeling successful.

But, looking back, I can see that the moments when I felt more free weren’t because I figured it all out on my own or got it all right. There wasn’t 1 budget or bottom line. I felt more successful when I had more people to care about in my life. I had three more people I could ask for advice instead of going to Google. That’s what made me feel successful. Not getting it all right all the time, but knowing I had someone else to call.

Weekly Letters success successful