Beyond the Number

Keep Trying: How To Overcome Failure and Succeed in Sales (and Life)

Sam Arnold, Senior Account Executive, green smoothie connoisseur's Avatar

Sam Arnold, Senior Account Executive, green smoothie connoisseur


Doesn’t it seem like every salesperson is successful? It’s true, check out your social media feeds. Everyone is living the dream: promotions, vacations, beautiful relationships and even more beautiful cars. If you still don’t believe me, check out the resumes of job applicants at your company. Everyone’s an over-achieving, Type-A, killing-it, crushing-it, hyper-motivated shark!

So, why aren’t you?

Maybe you aren’t smart enough. Or maybe your company’s product is bad, your manager’s an idiot, and sales is a dumb career anyway. You really should’ve gotten your master’s. Time to Google “code bootcamps” again. Maybe you can swing 12 weeks without pay if you move back home for a while…

Does this sound familiar to you?

If so, I know what you’re going through. I went through it for the better part of four years. Key word: went. I came out the other end and you can, too. It isn’t easy, but it isn’t as hard as you think, either.

Most of us didn’t choose the sales life, the sales life chose us.

I graduated with a BA in Philosophy & Economics from the University of Alabama. My options after school were, uh, limited. I applied for sales roles because I did well slinging Geek Squad protection plans in college. It seemed like something I could be good at.

For most of us, we “end up” in sales one way or another with big ambitions and even bigger anxieties. Those first cold-calls and email campaigns are fraught with confusion and ego-killing missteps. Then, our egos rebound and inflate with our first successes. Meetings landed, sales closed, quota hit!

They say the worst thing that can happen to you when gambling in Las Vegas is winning early on. That happened to me in my sales career. I did very well. Number one producer, earning more than I thought was possible. This was, I thought, my new reality.

It was after this success that I started to form a real answer to the question, Why are you in sales? When asked by friends, family, and strangers alike, I started to say some version of: “Because I like being rewarded based on performance.” It’s exciting, I’d answer. I wouldn’t have it any other way. And at the time, I really believed that.

Then the wins became smaller and fewer.

Leads slowed down, the product had issues. It didn’t look like things would improve, so I allowed myself to be recruited to a new job with a higher OTE. The wins there were smaller still and even fewer. No one seemed to be doing well there. (Was I lied to in the interview?) I could stay put and hope for the best or I could jump again and also hope for the best.

Fast-forward to three years after my banner year in sales. I’d had multiple jobs by this point at companies that I either left because I didn’t think I could make it work, or the company failed right out from under me. I moved across the country multiple times to stay afloat. But now I was broke and living back home, selling copiers door-to-door.

It was the darkest time in my life and I had no idea how to turn things around.

I was a mess. I accrued too much debt to pay. I gained dozens of pounds. I drank too much. When I wasn’t walking the sidewalks of Birmingham, Alabama, with copier brochures and bags of chocolate chip cookies to hand out (my boss insisted), I was reading about my old life: Silicon Valley tech, software sales, and the successes of my former peers. It felt like I was staring into a window of what could have been.

As painful as it was to be on the outside looking in, I still did it. Part of me was pining for what I lost, part of me was watching for a way to get back there. I know now that there were many opportunities to do so, but I disregarded them as I no longer felt worthy. I felt like damaged goods. My 15 minutes had come and gone.

I will be forever grateful to the friend who extended a helping hand. I am deliberately not naming people in this piece, but suffice it to say he was a former boss and we had grown closer over, of all things, Facebook chat. He was at a new company and needed help. It wasn’t sales, but at the time I thought that was probably for the best anyway. It was a shot to get back into my industry, maybe the last one I’d get, so I took it gratefully.

I wasn’t living happily-ever-after quite yet.

This was technically a remote position but I was staying in Silicon Valley 75% of the time. I spent long periods alone in my hotel room in quiet reflection. At work, I still felt like I was screwing up. Interacting with others wasn’t going well. The work was tedious. Management seemed impossible to please. But gradually, the hours I spent in solitude each evening began to make something apparent to me: fear was in the driver’s seat of my life.

Remember, this is several years after my career peak and through the subsequent low points I was feeling insecure about myself, certainly, but the narrative I had internalized was primarily about other forces being responsible for my state: bad luck, bad companies, bad advice. I was bad too, I thought, but in a secondary sort of way. I was a passive recipient of “bad,” waiting for the “good” to come back.

Now, with time and emotional distance, I was becoming more aware of my pervasive feelings of fear and my memories started to revise themselves as a result. Were the managers who hurt me really that nefarious, or were they struggling to alleviate my concerns in a way I would find acceptable? Were the companies I joined all chaotic messes, or was I looking for my work to provide me with an unreasonable level of stability because I didn’t have it at home? Was I reluctant to get out of bed because I hated my job, or because I was staying up too late and eating like crap? The more I thought, the more obvious the answers became.

With the answers in hand, now I needed to take action.

I switched from remote to living in SV full-time at the end of 2017, now four years into my slump. I drove from Alabama and had several days of quiet contemplation alone. I don’t know what it was exactly that tipped me over the edge. Maybe it was spending an evening gambling with sales guys in Oklahoma City. Or watching the stars in Sedona, Arizona. Maybe it was the conversations I had with beach bums in Morro Bay on New Years Eve.

Whatever it was, the net result was that on January 1, 2018, I decided I was done -- totally, completely done -- being an angry, world-hating loser.

I started on YouTube. Motivational videos: Tony Robbins, Les Brown, Simon Sinek, and others. Whereas once I would have guffawed at the mere mention of these men, I was now weeping while listening to their speeches and cycling to the gym at 4:30am. I eliminated sugar from my diet, as well as alcohol, bread, and anything fried. I counted calories only occasionally to ensure I was eating enough. My goal was not weight loss, it was energy. I needed more energy to make the drastic changes I knew were required for my life. And a few weeks in, the energy started to emerge.

Waking up was easier now. I looked forward to my green smoothie each day. The mental fog was lifting. My moods felt more balanced. Avoiding alcohol was hard at times, since all socializing basically revolves around the stuff. But I stuck to my guns. Moving my body each day was important to me now. If I couldn’t get to the gym, I walked around town -- over 15 miles a day on some weekends while listening to motivational videos and audiobooks, planning my escape from the hole I had dug for myself.


I needed to get back to sales.

Despite my previous failures, I recognized how important it was to get back to a commission-based job. It was the first truly clear-eyed, not-fear-based life decision I had made in years. I was good at sales, damn it, and I did enjoy it. I did not like earning the same paycheck week after week, with only the promise of a meager annual raise on the horizon if I was lucky. So, when I spotted an opportunity and vetted it thoroughly, I took it. I was back in sales by late February.

I won’t lie and say my transition was an easy one. I didn’t arrive at the company a well-adjusted Superman. There were still rough edges to be filed down. My fear was present, albeit smaller and more controlled. I had some hard talks with my new manager during my first couple of weeks. Was I happy here? Was I able to roll with the unique punches that happen in sales? Even a few months earlier, the answer to those questions would have been “no.” I wasn’t ready then. I wasn’t self-aware enough to take emotional inventory and sort myself out. But now I was.

Changing oneself is hard. It’s painful. The approach I took was a logical one: if what I wanted to do made things worse, I should do the opposite -- what I don’t want to do -- to make things better. When I became afraid, instead of avoiding thinking about it or trying to seize control of everything around me, I leaned into it. I felt it. What exactly was I afraid of? What’s the worst-case scenario? What will I do if it happens?

The answer to the last question was always the same: Keep trying. I’ll just keep trying! If I fail, if someone hurts me, if I lose everything I have, the answer will always be those two words. It became my affirmation, my mantra. Even today, when I feel fear of failure bubbling up, I remind myself: So what? Failure will not change my plan whatsoever.

No matter what happens, the plan is always the same: Keep trying.

Simple. Beautiful. Fear, I realized, comes from not knowing what to do. But if you always know what you are going to do -- keep trying -- the fear melts away. Your plan is set. It won’t always go your way. In fact it rarely will. So why worry? Just keep trying.

Something good must have happened after I changed my mindset, right? Otherwise I probably wouldn’t have written this post! Indeed, some good things did happen between March and December of last year:

  • Q2 (my first quarter) I was technically on ramp and achieved over 500% of my goal. We ended up nixing the ramp for me, and I ended over 200%.
  • Q3 I achieved over 800% of my goal.
  • Q4 I achieved over 360% of my goal.
  • I was the #1 salesperson in each of these quarters and won President’s Club.

The worst of my problems, both personal and professional, have now been solved. I thought it would take me years. It took six months.

Yes, I got lucky at times. Really lucky, no doubt about it. But isn’t it strange that this luck only started happening after I took dramatic steps to change my mind and my health? Is that a coincidence? I don’t think so.

I have never been more excited about life than I am right now. My life is far from perfect and there are other areas that still need a lot of work. I still screw up about as much as I always have. Fear still holds me back from time to time. But now I know what to do, how to handle myself, in good times and in bad.

Keep trying.

If there’s one takeaway I hope you get out of this, it’s that one. Just keep trying. At everything. Don’t give up, don’t look for easier paths, and don’t let yourself believe you deserve anything other than the very best in life. Change is not only possible, it is inevitable. You will change over time no matter what you do or don’t do. The nature of that change is up to you.


Sam Arnold is now a Senior Account Executive at CircleCI, where he has thrived, been promoted (twice), and achieved President’s Club in less than one year.

Sam's story is part of the Outreach Beyond the Number series, celebrating the human side of sales.