Reflecting on a career in Sales- many failures and success

Thoughts on failure, sales, and success

I’ve failed many times in life. There were moments where I had a former manager suggest that perhaps a career in sales is not for you. I remember feeling so defeated when I was let go because I was honestly not pumped about the product. The advice I typically give to younger sales professionals who reach out to me for advice is to 100% believe in what you are selling. Many younger folks usually respond well, I’m not even sure what I really like. I made the mistake of following the money, and it usually didn’t pay off. I’ve learned that I enjoy with Learning and Development professionals through working at LinkedIn Learning. Anyone who knows me was not surprised that I would leave LinkedIn, which is an incredibly difficult company to get into for a smaller start-up. CoachHub has been one of the best decisions I’ve ever made right off the bat because I never been more excited for anything else in my life. 

Coaching has been one of the most significant factors in my life in my recent success. I went from being depressed, sad, and did not have a strong career to having a life I couldn’t even imagine five years later. It wasn’t easy… I went through so many stages trying to find myself hopping from job to job just following the money. Fortunate, I’ve met some incredible people along the way, and many managers took a chance on me because there saw something in my character. Even though a sales professional’s life is not always easy, I would say it’s quite hard. I think of it as a professional athlete, because you show up to practice every day even if you don’t “feel” like it. You know the reps will ultimately make you a better person. It’s not cut out for everyone, and I would say that is probably one of the most demanding career decisions you will ever make but one of the most rewarding decisions ever. You will be able to meet so many incredible business owners. You will meet people who want to solve many world problems, and you will also be surrounded by some of the most competitive people ever. Some of them are collegiate athletes, and many of them sick enough to subject themselves to a world of torture. Yes, some risks come with the profession like so days you feel like you are eating ramen noodles and other months where you’ve put down a down payment for your house and just purchased a new car. 

Some of my sales career highlights have been more of when I have been mentoring and coaching younger reps in their career decisions. Because you can never truly master the art of sales, it’s one of the professions where even if you spend 10,000 hours, you can continuously improve and get better every week. Because things are constantly changing. That’s what makes it so exciting. With the invention of technology and resources like leveraging LinkedIn. You have to adapt, and this is the top 10 advice I would give to younger sales professionals since many have reached out to me to want to learn more about what it takes to be successful in sales.

  1. Educate yourself, and don’t be afraid to try new techniques. Everyone has their own unique style, and that’s what makes the beauty of sales so interesting. One person can be highly data-driven and calculate how many emails they need to send in order to reach their number. I’m more of a relationship builder, so I truly get to understand my client outside of their business. 
  2. Making sure you don’t try to do everything on your own. There have been so many instances where I felt like, oh this other top rep is quite busy. I don’t know if I should reach out to them because they probably have so many other reps reaching out to me. When I speak with them, they always say no I think everyone has that same mentality so I actually don’t get reached out as often as you think. Being able to pick the brains of the great sales professionals I’ve worked within the past in Zack Mulhall, Andy Linder, and many of our large enterprise reps have taught me how similar we are. It’s always helped boost my confidence. We are often our most prominent critics. 
  3. Don’t be afraid to take chances. Many would take a superficial look at my career and say things like why you would ever leave a company like LinkedIn that is consistently ranked one of the world’s top companies to work for. Statistically speaking, we have the top 5 average salaries out of every company in the world. But I knew deep down in my heart that going to CoachHub is the right decision for me. Some have even said it’s the honeymoon stage, but I genuinely have never felt this excited about selling any product. Your mission in life is 100% aligned with the company’s mission there is no room for failure. Of course, I’m not perfect, and sales itself is messy, but I know that I will be successful because I truly believe in democratizing coaching for millions of people. To be a vital part of that in the US market and be one of the first reps is such an exciting opportunity for me. 
  4. One of my mentors used to say: make sure you always make the time to give back. I never understood what he meant by that because I always told myself I would never be that guy who doesn’t get back to people. Now he’s making me swallow my words. Being a giver, I love helping people, but I never imagined that I would be getting hundreds of reach outs every month. This is quite overwhelming and one of the reasons I’m writing out a lot of my tips for success so that I can scale my impact. It’s truly a blessing to be someone who gets to help so many people but now I know what Alex Metz is referring to.
  5. Don’t be afraid to put yourself out there– there are going to be times where you make mistakes and you say something that doesn’t work out. It’s okay, we all make dumb decisions sometimes and give yourself grace that things that don’t always work out, but those tend to be the lessons that you can look at 5 to 10 years from now and are glad you made those mistakes. You tend to learn more from the mistakes you make than all of the success. I think that’s why I have been so successful in my career because I feel like I’ve made many more mistakes than most people.  
  6. Network, network, network. It’s one of the beautiful things about our job. What other career can you meet someone new, every single day. It’s a beautiful thing to step into the life of another person. It can be also be overwhelming if meeting and trying to understand someone else’s world does not give you energy. Fortunate, introverts make some of the best salespeople because they allow the other person to share without interruption. The older I get, the more introverted I become because I was so focused on other people I realized that I also needed to be extremely curious about myself. 
  7. Don’t forget to take the time to learn about other departments. Being curious about your counterparts in finance, customer success, account management, project management, client services, etc will always serve you more than you think. Because us sales folks are always asking for help. When you take the time to get to know someone, and you aren’t always asking for something. They are much more likely to help you out. Give and take is an interesting concept that I didn’t think too much about before going into the professional world but I’ve been fortunate because I’ve given so much that I generally don’t feel bad about asking for help/support.
  8. Writing thank you cards– one of the lessons I’ve learned from reading some of the most successful sales professionals in the world is how much time they put into truly acknowledging the person in your life who have made a difference. By continuing to build these relationships you always have someone to call if you ever need support or have a question. It just makes you feel good and its something small that can make someone’s day. 
  9. Try that thing that scares you the most- I am deathly afraid of rejection which is funny because everyday I’m getting rejected at work and it still hard to get rejected and not take it personally. You think from being in 18 years of sales that it would get easier but if anything it gets harder because I still have an ego and sometimes when you get older you think so much about your professional brand. I would recommend always diving into the thing that scares you will often give you the most growth. 
  10. Have fun– Sales is an interesting beast so gamifying the experience will help you have a longer career. I feel like its possible to have fun once we gamify the milestones that we have. It’s always a lot more fun to prospect with your colleagues even if you are just on zoom and aren’t really saying that much its more fun to do it with someone else. The shared pain always makes experiences a lot more enjoyable. 

Well I hope you enjoyed this spur-of-the-moment reflection. It’s good to take the time to reflect and hopefully, this inspires at least one person to consider a great career choice that has a load of potential. 


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davidsonhang View All →

Purpose: I create an empowering context for curious and hungry people looking for fulfillment, experiences, and creativity. We do this by developing their growth mindset, introducing self-love, and powerful group experiences. It results in people with strong boundaries, resilient mental health, and practical life skills

People leave with the ability to land their dream job, have autonomy and flexibility with their lifestyle, travel the world, and create from their heart and soul.


Davidson was once broke, insecure, low-confidence, and frustrated by doing all the wrong activities. Addicted to drugs, validation, and wallowing in self-pity. No relationship to family, and at the mercy of other people’s suggestions and opinions.

It was hell.

After spending $100k hiring different coaches, traveling the world doing workshops around the world, reading>1000 books, and through curiosity, have created the most effective system to remove people from that situation. My life’s work is to bring joy and abundance to people who as on a similar path as I was and bring back the joy and abundance of their life.

Through shared experiences and storytelling, I inspire and model behaviors that lead to a richer, more fulfilled life full of joy, experiences, passion, and ecstasy from the richness of relationships and being able to experience the depths of the human experience.

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