If you couldn’t tell, I’m obsessed with running. Throughout the years, running has been my mental lifeline, particularly in some of my darkest moments. Running has also brought about some of the most impactful ideas and lessons I’ve been able to apply to life. While running shorter distances are powerful for freeing my mind to ideas, I’ve found that the longer distances are what have pushed me beyond the normal limits of mind and body.

Leaving the safety of a “typical" job and venturing off on my own has had similar affects and parallels to what I’ve experienced running marathons and ultra-marathons. This post is both a reminder to myself and motivation to others. The scariness and uncomfortableness of stretching yourself beyond your limits is normal and necessary.

Training is essential - Let’s face it. Anyone can do anything without the proper training. For shorter races, lack of training is inconsequential because you can always walk to the finish line if you can’t run anymore. But if you want to finish any race still running, you have to train, especially the longer distances. When you get into ultra-marathon distances, like 50 miles plus, training (or the lack therefore) is the difference between finishing or being disqualified.

I’ve been working with startups for 20+ years and have experienced both successes and failures. After the most recent acquisition of Simplecast to SiriusXM, I felt like I had enough skills to break off into freelancing.
You’ll never train enough - There comes a point at which you have to switch from training to doing. Fear of not being ready and the possibility of failure is the biggest blocker to doing anything. It’s so easy to never go beyond the training. My journey in life and running has always been to ask myself what is the worst thing that could happen if I pushed myself to do something new. In almost every circumstance the worst thing was damaging my pride and ego 🙃

Fear has always been my biggest hindrance in life. This was the year that I realized that wasn’t going to let fear hold me back anymore. I have all the skills necessary to succeed. I’m surrounded by people who want to see me pursue my dreams regardless of outcomes. Failure might occur, but I’d rather fail and try again, then never try at all.
Be strategic - There is more to a race than just following the course. You have to be strategic. You have to know when to fuel, how much to fuel, how fast to go, when to go faster or slower. Aside from training, strategy is the next most important thing to prevent yourself from sabotaging your race. My first race I knew nothing about strategy and I suffered for it. Strategy is also specific to the runner. There are best practices, but it’s also fluid, something that needs to be continually refined.

I’m not sure I was as strategic as I could have been with launching off into my own thing, but I had a plan. I spent hours refining my website and how I wanted to present myself. There were people I wanted to reach out to to get advice and also make connections. It’s been a month and a half and I’ve exhausted most of my contacts. I’ve learned that I wasn’t as prepared as I could have been, but I’m refining my strategy and pressing forward.
Take it steady - The biggest mistake that most (all?) runners make when running their first race is starting fast and too strong. If you start too fast at the beginning, especially longer distances you will burn out at the end. In almost every instance, starting slow and increasing pace towards the finish is the best and most optimal way to run a long-distance race. Pacing is critical, otherwise you will burn yourself out too soon and far from the finish.

For me I needed to be measured in the work that I took on. While I felt like I could do literally everything, I didn’t want to bury myself so deep that I was hating my life and not completing anything. I also wanted to see how I could balance paid work with personal projects.
Just keep moving - Never stop. Always, and I mean always, keep moving forward. Even if you are walking. I have burned out, because I went too fast at the beginning, but walking fast, or running very slow is surprisingly affective to finishing the race. Stopping will kill your time, momentum and mental state. Just. Keep. Moving.

Yup, I feel this literally every day of freelancing. Most days I want to quit, but I keep moving forward. I keep investing time into people, projects and blog posts like this. It will pay off, I just don’t know when. I’ve had a couple paid projects, but not enough for this to be sustainable, and yet I keep moving forward.
It will hurt, bad - You will want to quit. Everything in your body and mind will be screaming to quit. You will be questioning your life choices. You will be thinking about how easy it would be to stop and get a ride to the finish line. Every race I’ve run I’ve wanted to quit. The problem is that if you quit, you will regret quitting. Just don’t.

So when should you quit? When you physically cannot sustain any forward momentum. For this entrepreneurial “race” I’m on, it’s when I cannot monetarily sustain forward momentum.
You are not alone - While running races are mostly about pushing yourself and seeing what you can accomplish, there are lots of other runners who are doing the same thing are you. They are also going through the same kind of hell as you.
Receive help and advice - Races, marathons, ultra-marathons, life have all be done before by experience people. Lean on those who have gone before to help you. Races also have aid stations and people who can be sources of encouragement along the way. One ultra that I ran, I wanted to quit, but the aid station people calmly and gently helped me get my mind and body back in the game and I finished the race.
Know where the finish line is - There is always a clear finish line with a race, regardless of the distance. Knowing where that line is important. It signifies you’re done. It signifies you’ve accomplished what you set out to do. What is your finish line? In a race it’s clear, in life, a little less so.

With Simplecast, I didn’t know where my finish line was, so I kept on going long after I should have. I was already spent and then continued to burn myself out. Acquisition and some padding after that should have been my finish line. Instead I spent three years in big company culture at SiriusXM trying to make it work, but I’ll save that for another post.
You will fail - Most people see failure as the worst thing that can happen in life. But the reality is that failure is inevitable in literally every aspect of life. How you fail and your response to failure has everything to do with future success.

I might fail. I’m ok with that reality. I would rather fail than forever wish I had tried.