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Update Your Ambition Every 6 Months And 21 Other Pieces of Career Advice

When I first started my career, my oldest brother Travis (now CEO of York Creative Collective and Investment Partner and Advisor for York IE) gave me some sound advice. It made a ton of sense back then, especially early in my professional life, as I was still unsure what I wanted out of my career. “Make sure to update your resume every six months. You never know when opportunity will present itself and you need to be ready.” Back in 2013 while building Dyn, our exec team went on stage at a company meeting and addressed the group about setting aspirational goals, goals that seem so ludicrous and into the future they couldn’t possibly be attainable. I shared this story as we challenged our entire company to think BIG on our quest to play an integral part in the workings of the Internet (yes, the whole thing). We had that much potential in front of us. “We want to be able to run the entire Internet on our services,” we said. “If THE INTERNET calls, we need to be able to say yes.” Well, it certainly played out that way as we scaled the company to $100M ARR and 5000 enterprise customers the likes of Amazon, Shopify, Netflix, Spotify, Bloomberg, Fastly, The New York Times, eBay et al, which ultimately led to our eventual acquisition by Oracle. We ran the internet. I’m certainly glad I joined Dyn as employee 15 in late 2008. Like my career, my brother’s advice evolved with continuous tweaks along the way. Once you find the foundation to truly change the world and have a crazy impact in your professional life, I encourage you to dream big and “update your ambition every six months.” That’s what we did in coming up with such an ambitious statement like the one above at Dyn and it’s certainly what we’ve created in York IE as we look to reshape the way startups are built, scaled and monetized. It’s always easier to simply try to replicate successes achieved over the past six months and say, “Good enough.” However, we’re not in our careers to walk to first base. We’re in them to hit a grand slam. From a personal and professional standpoint, where are you at today from where you were in 2013? Where you were six months ago?? Where do you want to be in January 2021? What about a decade from now? What about at the end of your illustrious career? Are you dreaming big enough?

Along with that, here is some other career advice that I’ve learned to live by through the years:

  1. Create a career narrative → Does your career arc make sense? If not, tighten up your personal brand and personal pitch. People can relate to a good story.
  2. Set aspirational goals → If you set goals that are easy to attain, are they really goals or are they just milestones on the way to a larger journey? It’s important to constantly challenge yourself.
  3. Think strategically → I find that most people lose perspective and often get disconnected from a grander strategy because they get buried in the weeds. Always take a step back and ask yourself what contribution you’re making and how it fits into the grander picture.
  4. Fit yourself into your company’s story → Like the career narrative, how do you fit into your company’s story? It’s important that you can weave yourself into your company’s pitch and share that with people you come across.
  5. Adapt or die → This could never be more true than in a technology company or a fast-growth business of any kind. Change is the only constant you’ll see. If you aren’t prepared to adjust, you’ll get left behind. I’ve seen this firsthand (not literally!).
  6. Draw the line (on what you know and don’t) → Most people have a hard time clearly drawing the line between what they’re supposed to know and what they aren’t. It’s a must to nail this and be comfortable with that clearness. It should not be vague.
  7. Leverage your resources → Once you nail the above, then you can pull in peers or mentors and collaborate to accomplish big things.
  8. Build complementary teams (or be a complementary piece) → I know I’m not perfectly organized or detail oriented. I am brutal with math and numbers. I have teams around me that compliment me and I compliment them. Org development is all about team.
  9. Always self reflect (be self aware) → Part of each one of these points is to really know yourself. If you don’t know what you’re good at or what makes you happy, you’ll never be motivated and you’ll never be successful.
  10. Find your hooks (in your work) → These are all blending together, but can you say you’ve figured out what gets you out of bed each morning? Business model? Technology? Professional development? Team? Market? Think about it.
  11. Focus on strengths & level up the weaknesses → Run a strength-based org, especially as you grow. Ask your people to lock in at what they’re epic at. When it comes to weaknesses, do your best to make them less weak.
  12. Iterate before failure → Former New England Patriots quarterback Tom Brady always talks about the mistakes he’s already made in his career and how those allow him to make less today or make quicker decisions to right the ship.
  13. Exude passion → This is all me. I’ve always had an ability to take serious intrinsic ownership over my work and career (and personal life). I care more than the average person and I dive into everything I do.
  14. Be empathetic → Richard Branson best summarizes empathy and I’ll listen to everything this business mentor of mine shares. I admire the “put yourself in their shoes” approach.
  15. Never stop learning & always be a sponge → It’s important that your ideas are a cross-section of the ideas and experiences you learn from others, blended with your own instincts and experience. Be the most prepared person in the room.
  16. Prioritize → This is often learned the hard way. Not everything you do is of equal importance or of equal timeliness.
  17. Define what you can control and influence -> Former colleague John D’Amato taught me a lesson on buckets of control that changed my perspective on focus and priorities.
  18. Have conviction and confidence → This is where leadership is earned. Don’t be indecisive or people will see it as weakness.
  19. Be deliberate in communication → Communication is key to every single decision made in a company. It’s the most important aspect of a growing company.
  20. It’s the principle of the thing → As a kid, my dad always talked about this, something I speak about frequently and live by. Be principled.
  21. Play the long game → And as always, have a vision and execute feverishly day in and day out to get there over the long haul.

For more career advice and an in-depth explanation of the core business principles that can help shape your career, download our eBook!

*An original version of this post was shared on back in 2013, seven years ago.

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