February 13, 2020

Breaking Into Tech: 7 Lessons Learned After 472 Days of Risk-Taking & Embracing Failure

TL;DR — This isn’t a self-promotional post about landing a job. It’s about embracing failure and hard lessons as a necessary part of the process in making a lofty dream become a reality.

These days when people ask me how I’m doing, I would often ask if they’ve seen “The Pursuit of Happyness” because life for me is like the movie (mainly the ending). Through the pursuit of my own “happiness” — I learned valuable lessons in making a dream become a reality.

Imagine celebrating your birthday with family and friends while on vacation to then face an untimely career setback all in the same week and now asking yourself what do you want out of your career but, more importantly, your life?

Real questions yield real answers, and I’m here to tell you that transitioning from where you are to where you want to be is hard, but it’s not impossible. It took me 472 Days. A whole bunch of “No’s” and one “Not Yet” that eventually became a “Yes” to make my goal of pivoting to tech become a reality 

Instead of “flexing” my latest win on social media like a millennial, I wanted to be impactful and share the learnings I’ve gained throughout my journey.

The Back Story: Exposure Gave Me Inspiration

For two years (2017 & 2018), my friends and I attended AfroTech, and I was blown away by the amazing people I met who looked like me and were living out their dreams doing meaningful work in tech, which inspired me.

In June of 2018, I attended Spotify’s one day conference in partnership with AfroTech. I went to that event with an open mind as I was interested in learning more about the intersection of music, tech, and culture. I left that conference telling myself that I could see myself working at Spotify.

I didn’t know after leaving the conference that I would soon embark on an emotional rollercoaster filled journey that taught me valuable lessons that required me to unlearn, reprogram, and shift my mindset to achieve my goal.

I want to share my experience in hopes of inspiring all the first-generation kids out there who grew up placing an unhealthy amount of their self-worth in their professional accomplishments. For the kids who want to be “successful” as quickly as possible to impress their families but feel terrible any time they fail at something. Stop putting so much pressure on yourself!

Stop living in the past. Stop being anxious for the future. Focus on the here and now and in the words of my 11th grade English Honors teacher Mr. Kurtzer,

“Always make decisions for which you can like yourself.”

Here are seven gems I learned along my journey to accomplish my goal of breaking into tech. I hope it inspires you to go beyond plus ultra to make your dream become a reality.

#1 — Take Risks. Regardless of The Outcome, You’ll Always Win

If you want to live the life you want instead of settling for the life you’ll get, take a risk. Calculated or not, the outcome will bring you two things. An accomplished goal or a lesson learned. Either way, you win so… why not?

“A loss ain’t a loss; it’s a lesson.’’

– Jay Z

That was my mentality when I took a calculated risk to leave a contract job on the verge of becoming full-time to pursue my goal of pivoting to tech. To some, it sounds crazy, but to me, a risk-averse person who played it safe his whole life. Making that decision with no backup plan was the biggest risk I ever made! I knew if I didn’t bet on myself and go all-in, I’d regret it.

How I Applied It: I made a goal of landing a job in tech by my 25th birthday. I didn’t achieve it, so I adjusted my plan and exhausted all of my resources, and three months later, I made it happen.

#2 — Shift Your Attitude Because You Have Everything You Need

Change the way you look at things and the things you look at change. I had to change my outlook and stop feeling desperate to land a job when the pressure got real.

Two books I read that helped shift my perspective about my career journey were ‘Strategize to Win’ and ‘Let Them See You.’ Before reading those books, I wanted to secure a “sexy job” to impress and stunt on people to get validation. When I realized my “WHY” was tainted, I made the adjustments to align my job search with my values and skills I wanted to gain. Once I made that shift thing changed for me.

How I Applied It: I told myself to trust the journey I was on and to embrace all the opportunities that would come along (speaking engagements, new relationships, etc).

#3 — Embrace Failure, It’s The Best Coach You’ll Ever Have

Adversity introduces you to the real you. When things don’t go according to plan instead of being upset and giving up. Follow this three-step framework:

(1) Identify the mistake (2) Learn from it (3)Apply the learning

After going on countless interviews and getting the same outcome I doubted myself and questioned if I was cut out for this industry. I started asking myself “If I could do this over again what would I do differently?” Asking that simple question started my journey of embracing failure. When my relationship with failure changed so did my outlook on life. If you’re not failing, how are you growing? Failing teaches you to be better for the next opportunity because they’ll always be another opportunity.

How I Applied It: I adopted a growth mindset when it came to failing. I welcomed feedback and used it as fuel to get better and improve.

#4 — Overnight Success Is A Myth. Work for What You Want

There’s no such thing as an overnight success. Accomplishing anything worthwhile is a step by step process that can’t be cheated by taking the elevator. You gotta take the stairs!

I knew my goal of pivoting to tech wasn’t going to happen immediately. I knew it was going to take time but I never imagined it would have taken me 15 months of rejection to accomplish. A lot happened in my personal life from the loss of family, emergency hospital visits, and battles with anxiety that made me realize that life goes on. When experiencing the trials of life you have to stay the course and keep progressing towards your goal.

Be intentional and self-disciplined in whatever you set your mind towards accomplishing. The elevator shortcut to success robs you of the experience. It’s not in the destination that joy is found but in the process of working towards a vision you have.

How I Applied It: I became intentional and disciplined on the specific areas of my job search I wanted to improve upon and worked towards it.

#5 — No One Is Self-Made. Leverage The Power of Your Network

There’s no such thing as a self-made person. We all are where we are in life right now because of the grace of other people who helped us along our journey. Whether you want to give people their flowers or not — people need people, it’s just that simple.

To accomplish my goal I swallowed my pride and reached out to people. It was tough because I’m used to being the helper but this time the helper needed help but was too prideful to ask.

Honestly, my pride was a bigger hindrance than any non-believer (hater) could ever be. Asking for help was hard because I didn’t know the practical way of doing it without feeling desperate. I learned from a friend that you ask for help by simply stating the facts of your situation and how you would like to be supported.

How I Applied It: I leveraged the power of my network (mentors, career coaches, friends, etc.) to help me and I’m grateful they offered a helping hand when I was too stubborn to think I needed one.

#6 — Just Win Today

Do one thing every day to better yourself. I often caught myself romanticizing a version of my future glow up story but not embrace or take advantage of my current situation. I realized you have to actually LIVE your life to tell your story later. Don’t wait to pivot into your greatness. There’s no such thing as a perfect time to do anything. Just a set of ideal circumstances to take advantage of to better reach your goals.

“If you are depressed, you are living in the past. If you are anxious, you are living in the future. If you are at peace, you are living in the moment.”

— Lao Tzu

After seeing this quote, I became intentional in the daily tasks I needed to perform to improve my situation. That way of thinking birthed my mantra “Just Win Today” which reminded me that to accomplish any goal I had to control what I could control and that’s my thoughts, actions, and habits. The compound effect of sticking to this routine allowed me to make marginal returns that ultimately helped me accomplish my goal.

How I applied it: I took inventory on how I spent my days and challenged myself to accomplish three specific tasks each day in pursuit of bettering my situation. Practicing interview questions, going to the library to avoid distractions, and journaling to track my progress.

#7 — Trust Your Struggle

When you think you can’t go on anymore just remember your why. Trust the storm you’re facing is necessary to shape you into a better version of yourself.

I realized that I was going through a long job search for a reason that was bigger than being unemployed. There were several lessons I dubbed “Hard Truths” that I had to learn about myself, family, and faith as LIFE was clearly happening to me.

“If There Is No Struggle, There Is No Progress”

— Frederick Douglass

It pains me to say this but failure is a huge part of success. Sunny days wouldn’t be special if it wasn’t for the rain, joy wouldn’t feel so good if it wasn’t for pain.

When I kept facing rejection I started to wonder if I was aiming too high. I began to doubt myself as my energy and efforts weren’t leading me to my desired results. I realized I couldn’t quit and lose. If the plan doesn’t work change the plan not the goal. The most uncomfortable time in your life always happens right when you’re about to have a breakthrough. Leveling up isn’t easy, but if you aren’t getting better by definition you’re getting worse.

How I Applied It: I watched Transformation Church’s Marked Series and used my “WHY” to stay true to a promise I made to myself after committing so much of my time, energy, and resources towards accomplishing my goal.

My “WHY” motivated me to see beyond my limiting beliefs and doubts. I believed my struggle would groom me into the person I’ve always wanted to be and looking back…I was right to trust my struggle.

Chadwick Boseman Delivers Commencement Speech at Howard University

If you’re interested in marketing, tech, and media or a part of a mission-driven collective connect with me on InstagramTwitter, or LinkedIn.

For anyone going through it, keep your head up and remember your current situation doesn’t define you or your life’s trajectory.


At the intersection of Media, Tech, & Culture. We each have our own unique POV. Here’s where I share mine.

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