The Long Ride — Strategizing Your Lifelong Career

How to avoid looking back with regret on your professional choices.
Inspired by the lessons in the book
The Long View by Brian Fetherstonhaugh CEO of Ogilvy & Mather, a 5,000 person creative agency with worldwide impact.

In my early twenties I realized I was unhappy in my job and career, so I made a change and started a business. A few years ago we hit rock-bottom and I had to re-evaluate my career and what I wanted to accomplish. I almost threw in the towel. It was not an easy task to redefine the goals of a failing organization, and turn it into a growing business. I think everyone struggles with the ability to zoom out and ask yourself — where do I want to go and how can I get there? I’m sharing these tips with you and my employees, in hopes to help us all achieve a happy, successful lifelong career.

Why You Should Strategize Your Career
The average retirement age is 63. That means that a 25 year old has roughly 4 more decades to accomplish what they want professionally. It seems that we forget that part and only focus on the zoomed in 1–3 year plan, overlooking the big picture of what we want in life. The average American also accumulates the majority of their personal wealth after the age of 40. Therefore if you’re not careful, you could be close to that age and look back wishing you had made the choices that would have afforded you a much better financial position in life.

If you don’t make a plan, you are less likely to get where you want to be. Marathon runners don’t win 26 mile long races by sprinting in the beginning. Prepare yourself for the second half of your life to get what you want out of the time you spent getting there.

It takes 10,000 hours to master something

Which is approximately 5 years of doing something everyday to become an expert and achieve an experienced position. Careers are created out of mastery and being that “go-to” person. What is it that you want to be known for? Mastery and expertise that isn’t only applicable to one job situation — transportable skills. Experiences that you can carry with you from one place to another. Mapping those skills that you hope to acquire can help you get the career fuel to power a lifelong journey of success — defined by you, the driver.

The 3 Principles of “Career Fuel”

Career fuel is what I used and had to build in order to stand out as a leader. You can do it too; whether inside an organization or as an entrepreneur.
  1. Transportable skills — these are things that you can take to any job in any career, and is stage one to building a fantastic future. They are things like persuasive communicator, a person who can get things done, a problem solver, a leader. The types of skills that employers seek out when hiring.

2. Create Networks of Champions — in the early stages of starting my company, I sought out a few individuals in Philadelphia who were successful at building businesses out of things that I was interested in. One of those individuals John Longacre, is the owner of a development company that is building a thriving neighborhood in South Philadelphia. John is one of those people who I share a similar values system with. In 6 years he has been one of the most influential people who has helped me grow, expand and build a mission-driven organization that has real purpose and impact. These are the type of people who you can ask them the hard questions that your self-help podcasts and books can’t teach you.

  • Tip — Create an eco-system of close contacts whom you admire

3. Ability to Ask for Help (and Give it) — When I hit my absolute lowest moment as an entrepreneur and almost lost everything I worked my ass off to create- I learned the hardest lesson — how to ask for help. As an Italian girl who grew up with a single mother for the first half of my childhood, I was taught how to be independent. So when I became a business owner, I was proud of my ability to do things on my own. Heck I built a business out of it! However when I needed help, my team and close contacts were raising their hand, waving it in my face volunteering their assistance. With hesitation and fear, I let them in on the problems I was facing. I was vulnerable and needed them more than ever before. And it was the most impactful thing that I did in our organization’s history. Practice small and you’ll soon see the changes when you’re brace enough to ask for help. Start some emails with “I need to ask your help”. Push yourself outside of your comfort zone and take a risk. Those meaningful experiences will help you build courage, which in return helps you ask for the assistance you need.

But how do I know where I want to go?

I’m asking myself this question again as well. Two years ago I stood in our 13th & Sansom Street Philadelphia office. It was empty, no furniture, no computers and no people. Back at our old office sat 5 employees who had their resumes out, ready to leave. I considered throwing in the towel. I decided to map out what I wanted to do next with the company which was build a mission-driven effort, a company with deeper purpose than making websites and logos for just any business. I wanted to build a team that collaborates, checks their egos at the door, and feels invested in their projects and the good it brings to the world. And two years later I can confidently say that we have achieved these things and more (we are 16 people now, tripled in size and I’m happy to report those 5 individuals never left and in fact became managers!). We are now growing a profitable business with a very impressive future.

Here are 4 questions to help build your career fuel

  1. How many contacts do you have? Size does not matter. It’s the quality of those people. No one looks back at age 55 and say to themselves; I want to thank all of the 1,300 friends I have on LinkedIn for helping me achieve my lifelong career goals. Make relationships with a handful of core people who are impactful in the industries you want to serve.
  2. What do you want from your professional career in the long run? When we rebrand a company, we create a strong strategy around their goals and objectives. A strategy is “how” you’re going to get there and connects it to why it’s important. Knowing your why is the important first step to outlining how to get there. What makes you feel good about yourself at the end of each day? What natural skill set do you enjoy?
  3. What types of skillset building resources can you tap into? 3 days a week I wake up early and listen to a podcast that motivates and educates me (The Art of Charm). This has become a source of inspiration for how I lead my team regularly and what themes I want to explore. What are the types of things that are right at your finger tips, that you could start using right now?
  4. How do you want to live? Does a 9–5 satisfy you? How high would you prioritize something like fun? Could you thrive as a remote worker or do you need to interact with people regularly? These things will be challenged throughout your career and it’s important to know what makes you happy.

Finally, check back in on this at least once per year. You will surprise yourself at how much you achieved and inspire the year ahead.