Dear Millennial Entrepreneur: How to Think about Your Next Move – Analyzing the 5 year itch

When we were 10 years old, we were all asked by our aunties and uncles the age old question – “What would you want to be when you grow up?” Most of us respond by stating what our parents expected of us to be when we grow up. Most of our parents brainwashed us to think that we want to be a “doctor, lawyer or in some rare cases, an engineer or banker.” I don’t blame them because these professions seems to be the safe choice during the past industrial revolution. 

Unfortunately, within the past 10 years, more and more of the 2 billion millennials or 27% of the world’s population that were born between 1981-1997 have entered the workforce in this new information enabled and digitally transformed world. There are professions that never existed in its current form even 10 years ago such as digital product manager, social media specialist, venture philanthropist, developer relations and others. Also, it seems that more and more, everyone seems to be interested in either joining or starting a tech start-ups trying to chase the ranks of Musk or Zuckerberg.  Explaining even these life choices and potential challenges to parents probably will end up in your mind thinking that these conversations will end up with “I told you that you should have taken up medicine like your cousin.”

Because of this situation that there is no direct guidance from people before them, there is a whole generation that entered the work force that is just “hacking their way through their career” with mythical mentors that they see in video blogs, LinkedIn posts or tech crunch articles. 

Now, the millennial generation (which I include myself), are past the first job that they took because they were just interested in the paycheck, then moved to the second job because of the passion, and now looking at that “perfect job that marries both passion, purpose and profit.” Funny that these thoughts typically bubble up in years 2-3 in every job, and the urgency to move typically happens in years 4-5. I don’t know if you think this way, but seems that this is a chronic discussion among my peers my age. It seems to even be more complicated that most of us have to be "adulting" with kids, houses, commitments and ageing parents.

Just recently, one of my former millennial colleagues called me yesterday to ask advice on how to think about the next potential move in his early career. It seems that more and more to get a weekly ping on Facebook or Linked that goes something like this:

“It seems I love what I am doing, everything seems to go according to plan, I like the mission of the organization but it seems something inside tells me that there is something missing. I feel I need to grow more. What should I do?  How should I think about this?”

It seems that this isn’t just coming from my friends who are in the corporate side but it also seems to come from founders and entrepreneurs who are currently working in their start-ups. For an entrepreneur it is actually doubly difficult because you can’t even talk to anyone in your company. You can’t tell your board or investors because they expect that you are slogging away to increase their shareholder value.  You can’t tell your colleagues or employees because they might freak out and start finding other jobs during your process of figuring out your next move. 

There is always an internal struggle – what I call 3 balancing balls of life – and as millennials we want to make sure we get all right. The 3 areas are:

·       Personal – Maintaining and cultivating real relationships with family, friends, environment that you thrive. Spending time with the people that you care the most about.

·       Professional – The right job and opportunity that takes advantage of your strengths and not your weakness in an industry and company that you are excited about

·       Passion – doing something that means something to you, a problem in the world that you think you can help solve in your lifetime

This is the never-ending quest – to get this all right in a job or start-up or anything. And honestly, this balancing act is what gets people to get the 5 year itch.

While I myself sometimes struggle with the same questions and maybe even I haven’t really had the balance, I found solace in doing this one thing: INTROSPECTION. Yup, sorry seems like fluff, but here are some questions to think about when you find a couple of hours or a quick 3 day trip to the beach or mountain that might be helpful.

1.      Embrace the five year itch, and if you think of your life as a series of 5 year sprints, then write down your 5 years goals in all the 3 areas that I mentioned above – 2 for personal, 2 for professional, 2 for passion.

2.      Think about the past 10 years and understand what drives you – reflect on your life mission - what are these causes that you come back over and over again. The one that “sings” to you. If you want some reference, I wrote an article that might help think about your mission called the Dear World exercise that I learned in the CES Social Innovation Summit.

3.      Write down potential roles that might be good next steps for you but now asking the questions – which of these roles actually align with these 5 year goals that I mentioned in step 1 and actually helps me fulfil step 2.

4.      Share these thoughts with close friends or mentors that you can be honest and vulnerable that you are not afraid to “go deep” with and see what they say about this. 

5.      Experiment and act. A good way to explore is what I called is a “passion 20%” where maybe you can volunteer or help out an organization that you might be exploring as a potential career track to really see if it does fit your bill. What I found out is that many organizations and industries now because they want to attract millennials, hype up their mission, but its only when you are it could be all marketing fluff, so better to do due diligence before coming all in.

To be honestly, I am always in a constant cycle to do go through these steps and I still try to answer these key questions constantly so I am no expert or have achieve any nirvana, but I am hoping that by sharing this, it might help some of you that have no one else to talk to that they trust and who are struggling to find your purpose amid the day to day grind of the early stages of the millennial career.

Hope this was helpful. 

Have you done a something similar exercise, and what happened? Would love to know any other suggestions in coping with the 5 year itch.

About the Author:

Earl is a venture advisor and corporation innovation leader. He is currently in the R&D Team of a Fortune 50 technology company and has advised hundreds of start-up companies in his career. He is a Stanford MBA graduate and a World Economic Forum Young Global Leader. Find out more about Earl at earlvalencia.com and his blog at innovationphilippines.wordpress.com.