“I’m taking a new job. I’m leaving Text-Em-All.”
A few years ago, I could never have dreamed of saying those words. But there I was, sitting in Brad’s office, Text-Em-All’s Co-Founder and President, thanking him for the past six years together, saying that it was time for me to move on and do something new. The conversation was nerve-wracking. It was adrenaline-pumping. It was something I’d thought about for countless hours and days before realizing that, yes, it was truly time to close this chapter of my life and do something new. It was so final.
And yet… Here I am, writing this blog 16 months later on a Text-Em-All computer inside Text-Em-All’s offices, and I couldn’t be happier. If you’re reading this and thinking to yourself, “what the heck happened?” You aren’t the only one. But I’m getting ahead of myself. Let’s start at the beginning.
I can trace this journey back to 2017. It was a year of monumental change in my life. I was a 24-year-old celebrating two years as an Account Manager at Text-Em-All, and I was beginning to get new responsibilities at work. It was also the year I met the woman who would become my wife.
But what I’ll always remember most is it was the year I lost my dad.
When you lose someone close, you may find yourself reflecting on their life, the impacts they made on you, and the lessons you can carry forward. In that, I became conscious that my dad had spent a huge portion of his life working for a job he didn’t like, so he might one day enjoy a retirement he never got.
But that all started to change when I got the opportunity to take over Text-Em-All’s partnerships.
At the time, a huge meeting was coming up to discuss the future of Text-Em-All’s integrated partnerships. Basically, Text-Em-All integrates with other software so that our mutual users can use Text-Em-All without having to leave their other systems. It was an area ripe for growth and ready for someone to own. On the day of that meeting, I had to take my dad to a doctor's appointment, so I let the team know I was going to miss it but that they could go on without me. Brad gently called me aside and said they’d move the meeting to a time that would work for me. He said he saw partnerships as a large part of my role at Text-Em-All and that they could wait while I took care of my family. To paraphrase his words: ‘Work will always be here. Your family needs you now.’ That meeting eventually happened, and Text-Em-All’s partnerships fell under me.
As I’d soon find out, that graciousness from Brad was a defining moment in my career.
Here’s a speed round of how the next few years went from there:
Right around this time, Text-Em-All’s Co-Founder, Hai, announced that he would be spinning up our company’s very first Product Team. ‘Yes!’ I thought, ‘This is my path to moving into the world of product and design.’
After this announcement, I asked Hai out to lunch to express my desire to transition to this new team and get his thoughts on my goals. The lunch went well! I walked out thinking that Hai now understood where I wanted to take my career and that there was a potential fit for me on his new team.
What did I do next? Nothing. I waited for product opportunities to come to me rather than leaning in and working with Hai to try to go from Account Manager to UX Designer. Looking back, I believe this was due to a combination of inexperience, youthfulness, and inappropriate expectations. The transition wasn’t happening as fast as I wanted it to. Rather than leaning in and continuing to work toward where I wanted to go, I leaned back and began telling myself the wrong stories instead of being open and vulnerable. I hoped others would remember my desire to work on the product and make it happen for me. I was waiting for a solution to come to me.
One night, my wife and I are having dinner with a friend of ours. The topic of work came up, and eventually, we landed on my job and what I hoped to transition into.
Our friend looked at me. “Um, Jon, you know I’m a Product Manager at a Fortune 150 company, right? We are hiring a ton of exactly what you’re wanting to do.”
All it took were those two sentences to plant a seed in my mind that, over the coming days, began to grow into a plant that wrapped itself around my every thought. I couldn’t stop wondering what it would be like to work at a big Fortune 150 company with hundreds of people I could work with and learn from.
I was scared to make such a big decision. But there was one thing I was scared of more. I was scared that if I didn’t try, I would wake up and look in the mirror every morning wondering what if? When you have a feeling like that in your stomach, it’s extremely difficult not to go for it. If I didn’t, I felt that I’d be letting myself down. And so I made a call, and before I knew it, I was talking to a recruiter who was ready to line up my interviews to become a Product Manager. A month later, I was preparing my resignation letter for Text-Em-All and dusting off my business casual slacks for the new position.
You have to understand; at this time, we were smack in the middle of the Great Resignation. It felt like every day, I would see another connection on LinkedIn posting about how they’d finally made a change to their dream job and that they were living the dream making more money and taking on new responsibilities. The grass looked so green.
At the same time, I had been working at Text-Em-All for six years. It was my first job out of university. I’d done reasonably well here, but what if that was a fluke? I wanted to prove to myself that the success I’d had at TEA so far wasn’t just a happy accident and that I could be successful elsewhere, too. That type of thinking was the exact opposite of what made me so successful in the early days of my career. I stopped seeking to learn and grow, and honestly, part of me thought I had it all figured out. I can see now how dangerous that type of thinking can be when allowed to run unchecked.
Lesson learned: The more I learn, the more I realize I don’t know. Keeping that mindset and balancing curiosity with humility is something I hope I never forget from this experience.
There’s a twist, though: Had I not made the choice to leave Text-Em-All, I wouldn’t have developed a skill set around product management. I wouldn’t have learned what it was like to manage a team of 8 at this point in my career. Plus, I’d probably still be taking parts of Text-Em-All’s culture for granted after 7 years. I firmly believe that I’m a better employee, co-worker, and person for Text-Em-All because I left and learned these lessons, so it’s not as black and white as one might suspect.
There’s a lot to be said about how my new role went. At a high level, there was both good and bad to be found. There were things about the job I enjoyed, but as time went on, more and more of my role was not what I’d envisioned when I joined the new team. I found myself having to come to grips with this new concept of having to climb the corporate ladder. Call me spoiled, but I’d never had to play politics before or network to earn new responsibilities, promotions, or raises and bonuses.
But most importantly, my mental and emotional health was deteriorating, and, as someone who’s married, that wasn’t just affecting me anymore. This new environment was, at the end of the day, contributing harm to my relationship with my family.
In these moments, I thought back to my dad and the unhealthy relationship he’d always seemed to have with his work (having to work on vacations, travel 25 days a month, etc.) and how it made him feel. He did all of this to provide for our family, and I lack the words to convey how thankful I am to him for what he did for us. Having said that, I would have traded a summer holiday on the beach for more authentic time with him in an instant. Unlike many, I once had the luxury of working at a place I loved. Once you taste that kind of relationship with your employer and work, it’s hard to want anything else. And so, around this point, I started wondering just how much I had walked away from at Text-Em-All. Did I make a mistake?
Lesson learned: I realized just how heavily my work’s culture impacts me and, thereby, how much it can affect my family. It’s obvious now, but it looks like where you spend the majority of your waking hours actually plays a part in the health of both you and those you love.
With the realization above, I started to think back to Text-Em-All and its relationship with my family. Through all the hard times, Text-Em-All had not only been there as support, they often proactively helped make those times easier in a number of ways. Benefits wise, completely covering employee healthcare and unlimited PTO went a long way.
I also thought about the good times, such as our annual reviews. Those meetings where my manager, Brad, and I would sit down and talk about the past year and the years to come were always something I looked forward to, and not just for the raises that came with them. In those meetings, Brad and Hai actually wanted to hear about our families and how Text-Em-All was affecting them. ‘We want to be a place that doesn’t look at a work/life balance,’ I could hear Brad say. ‘Text-Em-All is all about work-life integration.’
Lesson learned: It took being in an organization where, after a year of being there, only a select few people knew my wife’s name to realize how much care organizations like Text-Em-All put into their employees. Sometimes, it’s the small things like the founders of your company remembering to ask how your sister is doing at her new architecture job that mean the most.
As I became increasingly aware of these lessons, one thought kept striking me: for the sake of me and my family, I need to find a place I want to be.
I started looking for new jobs, going through the application process, and preparing for interviews. Here’s the problem: I caught myself comparing every single place to Text-Em-All.
“Huh… should I maybe stop comparing and just go back to the real thing?”
After that realization, I spent every weekend for a month preparing my portfolio and a few case studies to help showcase all I’d learned in my time away. I poured everything I’d accumulated into that portfolio, daring to hope it was enough to earn a place on Text-Em-All’s product team. On my own personal D-Day, my work was sent off as I clicked “send” on an email addressed to Brad and Hai. My stomach was in knots. What would they say? How would I handle ‘no’ gracefully? What will they think?
Bing! A new email hit my inbox from Brad.
“Hey, Jonny! Thanks for sending this over. Let’s talk.”
Those next conversations transformed my hope into reality. But, before I was offered a position, Brad and Hai had to talk to Text-Em-All’s leadership team and the product team, I’d be working on to ensure everyone bought into the idea of bringing Jonathan Melton back aboard. From there, it took only a few short days before I could hug my wife, both of us smiling ear to ear, and whisper, “I’m back,” both of us knowing that I was talking about more than just going back to Text-Em-All.