Are You Successful?

When can you tell if you’re successful? What is success? How is it defined?

Yeah I just started this with some questions, most people end a post with questions, I’m going to start mine with those. Now stop for a few minutes and come up with some answers to those questions. Don’t worry this post won’t go anywhere, it’ll wait…

Nope, still waiting for you, take your time. Ok, ready?

There is no definitive answer to success, success means something different to everyone. Some people don’t even think about it, they just live day-to-day doing their thing and that’s fine. In a lot of cases probably beneficial for your mental stability.

I will start with what I thought success was and what I think it is now. When I first started my career I thought success was making the most money I could, rising up in an organization to a place of leadership, working long hours, having all the things I wanted and doing what I wanted. What I learned (for me anyway) is only one of those is true.

Doing what I want. That is success for me. It’s not money or fame, cars and houses. It’s not being in a position of power and having people listen to all those “important” things you have to say. It’s about having the ability to do what you want when you want, be who you really want to be. Live to be you and only working to live.

What I found was the more money I made, the more I wanted, the harder it was for me to be satisfied. All the steps I defined as being successful were achieved and I hated every minute of it. I was tied to work to the point where not much else mattered. If I didn’t feel successful in my job my entire life suffered. Yes I was that guy.

This was really hard for me to get past but I still remember the one defining moment that made me think “Shit, what am I doing this for?”. I was in leadership training in Baltimore when I worked for Tribune Company. It was a program they put up and coming leaders in the organization where you got to rub elbows with all the high-level folks in Tribune and talk about leadership.

At this time Tribune was being sold so for better or worse people were saying what they really thought. I got to have a drink with the Senior VP of HR and we got to talking. I asked him, how do you manage to be so successful at work and still have a good family life?

He answered, “You Don’t. Something has to suffer and it’s your family”. At this point I‘m confused. I was used to getting advice that would lead you to believe you can do both. Then he said “I look back at my life and remember all the soccer games I missed, the dinners, dance recitals and I think…Was it worth it”?

He sort of left me hanging here and I replied with “Well was it?” and he replied “No”. I was in shock, the most honest answer ever and I will forever be grateful for that. My family means a lot to me and I can honestly say I would have sacrificed a lot of my family time to be “successful”.

Shortly after that I left Tribune and starting working with start-ups. When I left I took a 47% pay cut to be happy again. My wife and I sat down did a pros and cons list and she decided she would work more so that we weren’t so dependent on my salary (thanks Anne). No amount of money is worth killing yourself over. Yes start-ups are risky, but tell me what’s not.

I decided I would work with products and people that make me happy. I have had the opportunity to work for Viddler, Plain (Barley & Unmark) and now Formstack. The past 5–6 years for me have been all about personal growth. I‘ve been very lucky to be able to work at the places I want, making a more than fair wage and being happy.

As far as the financial part of life, you have to really sit down and figure out what makes you happy (not successful). Is it getting that new “thing” every time it comes out or is it having more time to really do the “things” you want to do. I went from working in an office around the clock to working in my own office. I get to see my family a lot more, eat lunch with my kids every day, see my kids off to school and work on amazing products with amazing people.

All of these things make me a better person, not just a better father, husband or a better employee. A better person. Not a lot of people can say this. I am one of the lucky ones.

Everyone has to make sacrifices for work in your personal life, but they should be rare, you shouldn’t have to sacrifice everything for any company. In my opinion at that point you aren’t living your dream, you’re living someone else’s.

So at the end of the day, don’t ask yourself what you can do to be successful. Ask yourself what you can do to be happy and do that instead.