Tech IndustrySep 7, 2022
ToyotaADarkKnigh

Am I having a Jerry Maguire moment?

I recently resigned from a TC:350 role with nothing secured and while I don't regret the decision, I feel forced to rethink my entire career. I've worked across the broad spectrum of digital for >20 years. I have no degrees or formal education, which has been a challenge at times, and I realize has set me back overall. I absolutely love learning new skills, and go deep in many. While this has proven helpful in opportunity development, it has diluted my value proposition on paper. Despite that, I've secured or ascended to leadership roles across each category (Dev, Mktg, Strat, Creative), and founded a small agency for years. As a result, I've cultivated a highly unusual composition, which I feel blessed to have and serves me well in any category. ...Until it doesn't. The Crux: - The employers interested in my scope couldn't do the things. - The employers who could do the things are not interested in my scope. I realize this isn't unique to me. But the more I see, the more I feel. I'm incredibly protective of the user, considerate of my teams, committed to the integrity of our work, and considerate of the opportunities to the business. And so my tolerance for conceding on either side is soon exhausted and I move on. The end result would be a career that is all over the board; Sr. Developer > Creative Dir. > Global Marketing Mgr > Innovation Mgr. > Product Manager > IT Solutions Mgr > Customer Experience Owner. And while each of these consisted of significant contribution and successes, my longest tenure is a paltry 3.5 years. I try to remain self-aware, which makes the reality of this very difficult. I'm not perfect, and waited too late in my career to learn the importance of being easy to work with. Please don't misunderstand, I never had issues with my teams or colleagues. But staying in my lane has often been a challenge, with the scale of impact typically correlating directly to that of the opportunity (*See 'The Crux'). I often wish I could care less. Not work all-nighters spinning up prototypes, circumventing friction, and overcoming internal issues. Not be constantly disappointed by leaders on cruise control or the lack of passion they've cultivated in their teams. More than anything, I want to work alongside people with the heart to do the hard things, for themselves, their team, or users they will never meet. I want to work with people who care enough to leave a bad relationship, and develop one that never puts them in that position. I want to work for an employer that considers Integrity to be an employee's greatest measure. I want to see somebody risk it all for the right thing. Maybe it's time to go solo, and accept the limitations that brings. Maybe I need to seriously rethink how I qualify opportunities. Maybe I just need to find a job that keeps my hands busy and my heart full. I feel discouraged, hopeless, and at the same time I am overwhelmed by options and a sense of obligation to push on. Just me?

Goldman Sachs ToxicBudha Sep 7, 2022

Toyota ADarkKnigh OP Sep 7, 2022

I understand. I'm getting on my own nerves today too.

Bloomberg RedRomeo28 Sep 7, 2022

Sounds like you should do management consulting

Toyota ADarkKnigh OP Sep 7, 2022

I appreciate that. But have to admit that my mgmt skills lack something to be desired. Mostly delegation skills.

Google looking4🍄 Sep 7, 2022

TC?

Toyota ADarkKnigh OP Sep 7, 2022

200 base, 150 stock

Microsoft Cleaner1 Sep 7, 2022

Who write long post in blind?

Microsoft zerometer Sep 7, 2022

Summary would be helpful!

Toyota ADarkKnigh OP Sep 7, 2022

I’ve spent a career trying to do it all. Impatience, a finicky EQ, and high standards have diluted my resume, which was already at a disadvantage due to lack of formal education. I’ve recently resigned from my job, based on convictions, and fear I’ll never find an opportunity that needs as much as I want to give. I’m lost. Defeated.

Grab wtsap Sep 7, 2022

Thanks for sharing OP. I believe you might be better off on the path to translate your principles and terms to your own business. Working for a company means you’re striking a deal with an employer that will always have their interests above yours, no matter how above and beyond you give them.

Toyota ADarkKnigh OP Sep 7, 2022

Thanks for reading! I wish I had done a better job at saving and felt better equipped to do that. And I still may. Thank you for the encouragement.

New
takada Sep 7, 2022

You’re not alone in this OP. The past 2.5 years were so unique and I know plenty of my friends, including me, recalibrated the importance work has in our lives. Sounds like you have the capital to take a “sabbatical”, use it to start your own gig. Worst case, you’ll find a new workplace in a year from now.

Toyota ADarkKnigh OP Sep 7, 2022

Yah. I’ve been trying to determine what is the least I can live on. I was a lot happier when I had less demanding roles, but time to explore and develop things on the side. Then I was less inclined to take out all of my ambition on my job, and had greater longevity. In either event, I agree… Time is key. Im glad you’ve been able to find balance!

Grab wtsap Sep 7, 2022

OP – one option to consider is taking a sabbatical as @takada suggested to geo-arbitrage. Move to an extremely LCOL location eg Portugal, Bali or Thailand (~USD2,000 / month for a comfortable living). Then, work on developing your business. Furthermore, if you’re a U.S. citizen and spend +330 days outside the US, you can be tax exempt for up to $112,000 on any income you make while living abroad. This — and living in an international LCOL — can become a lower risk to afford the time and attention to shaping your business ideas.