Navigating the Professional Journey: Embrace Change

There is a small minority of people (~20%) who know exactly what they want to do and pursue it with joy and satisfaction from early adulthood onwards. For most of us, the professional journey is filled with change. The average American has ~12 jobs in their career (a statistic from the Bureau of Labor Statistics on the generation just retiring.) Younger Americans will likely experience even more career change – by choice and by circumstances out of their control.

We still embrace the false notion that there is “a perfect job”  or “a passion I am meant to pursue” over a lengthy career. The reality is that, for most of us, this advice is misleading and sows both doubt and anxiety.

“We must be willing to let go of the life we planned so as to have the life that is waiting for us.”

– Joseph Campbell

Change is not just ok, but actually healthy and good. A core element of our life’s journey is to grow, develop, explore, and change.

And it’s perfectly normal not to know what is next. The career journey is filled with twists and turns, where new doors open when others close.

The CxO Community helps Members navigate and explore career transitions in a safe space. We help each Member make the decision that is right for them through a process of introspection and exploration.


Your Professional Journey: What Is Right For You This ‘Season?’

  1. We Believe in Seasons. Jobs tend to last 3 to 5 years on average. We encourage people to think in that timeframe. Nothing is forever. Picking one path for now will not close off others forever.
  2. You Know What You Want and Need. Our role in the Community is as guides to help you expose the knowledge that resides within you. We encourage you to trust your gut.
  3. Get Headed in the Right Direction rather than trying to pinpoint an Exact Destination. None of us know how things are going to turn out. But, we do know the broad parameters of what provides professional satisfaction. Those parameters will offer guidance on the direction in which to head.
  4. Explore what Gives your Energy and where you Find Flow. Every job has positive and negative aspects. Get familiar with aspects of your daily work that get you energized and where you find flow (defined as losing track of time while engrossed in a task.) Look for roles where these components are maximized.
  5. Quiet your Inner Critic. We all have an inner voice that shuts down ideas prematurely. Sometimes for good reason. But more often because we’ve been conditioned to tell ourselves what we “should” or “should not” do. The best way to select the right next step is to open yourself up to the plethora of potential opportunities, before ruling any out. You’ll be surprised by what you find could be possible and enjoyable.
  6. Talk with People and ‘Get the Story’. As seeds of curiosity begin to grow within you, we believe there you can satiate that curiosity and create a virtuous cycle that works for you. It’s all about being intentional. Lean in to your curiosity. Talk to people who do the thing you’re interested in. Not to get a job, or to get an interview, but JUST to get their story. You’ll learn more about the job this way than in any formal interview process.
  7. Prototype. We love the designer’s way of approaching work. Build something, test it and use the feedback as learning. Get creative in applying that principle to your professional journey. How might you ‘test’ an aspect of the job before either jumping in with both feet or ruling it out?
  8. It’s a Journey. One with no final destination, only wayfinding checkpoints along the way. Using these principles, you’ll be better equipped for the adventure and better able to enjoy all the twists and turns that are inevitably in front of you.
  9. Never Travel Alone. We were made to journey together. By traveling in community in your professional journey, you will never be alone. You will always have trusted travel companions and guides by your side, encouraging you through the valleys and celebrating with you at each mountaintop.


Evaluating a Specific New Job Opportunity

You have been asked to interview for a new role. Or perhaps, you are further along in the job search process and know you will get a job offer.

How should you decide if this new opportunity is right for you at this time?

Making a choice is a deeply personal decision. The important thing to remember is that you have choices.


Our framework for evaluating new opportunities is split into two buckets – the Business and the Job.


The Business.

Ask questions on the topics listed below and listen for how the employer answers them. Be willing to press (politely) for more comprehensive answers.

  1. The “Customer Problem”. What is the problem and why does this matter to customers? How well does the business solve the problem? Ask them how they know they are doing it well, and what the alternative solutions are for customers.

  2. The Market Size and Future Growth. It is easy to refer to market size statistics that sound both believable and enormous. Ask for bottoms-up data. Claiming an enormous market opportunity (i.e., the product works for almost everyone), particularly at an early stage, is a red flag to us.

  3. The Business Traction to date. Seek data such as number of (paying) customers, monthly or quarterly revenue, the growth trajectory of each of these and some measure of the retention rate.

  4. The Unit Economics of the business. See our piece on Business Acumen for a lot more detail on this calculation. It is crucial. If a senior executive can’t speak to this clearly, that is another danger sign.

  5. The Leadership Team. What is their mix of skills? Their level of experience? Is the CEO a founder or a professional manager? If a founder, is this their first time leading an organization? We look for balanced leadership teams with optimism (first-time) complemented by experience (been there, done that.)

  6. The Valuation and Runway (months of cash left before they need to raise money). Employers may not provide this data. We find the lack of transparency to be a bad omen, especially when hiring a senior leader.


The Job.

Evaluate what you are going to do. Learn about your manager and their style, Get compensation details. Understand what potential future growth paths look like for this role.

  1. Responsibilities. What exactly does the role encompass? Ask for some detail on the first 90 days. Inquire about how success will be measured or what the key goals are for the current year for the team you are joining or leading.

  2. Manager. In the long-term your manager is the most important factor in determining job satisfaction. What is their style? How might you fit with them, the company culture, and the rest of their team? Do you believe the manager cares about their team members’ individual success or mostly about their own success? What can you learn from this person (and would that learning be valuable to you).

  3. Compensation. Naturally important. Ensure you are fairly valued for your skills. Understand the mix of base salary, cash bonus and equity/option grants. Ask about compensation philosophy.

  4. Growth Opportunities. Inquire about career paths or where this role could lead over time. Is this an organization that tends to promote from within or add senior talent from outside? Is the hiring manager solving an immediate pain point or also thinking about the longer term?


Members Supporting Each Other

Navigating a career of 30+ years is challenging.  The CxO Community is here to help each other along the journey. We believe that if we put out into the universe the “energy” we want to find ourselves, that it will come back to us in spades.

Lean on me. When you’re not strong. And I’ll be your friend. I’ll help you carry on…

For it won’t be long. ‘Til I’m going to need somebody to lean on.

-Bill Withers

Aditya Dehejia

Adi’s experiences as a CFO and HR leader in start-up companies inspired him to start the CxO Leadership Accelerator. He saw firsthand the challenges in building a satisfying career, the importance of leaders in developing people, and the difficulty in building broad business acumen while excelling in your functional role. Prior to his operating career in start-ups, Adi held roles in a growth capital investment firm and in the corporate development and strategy department at a Fortune 500 company. Adi is an active volunteer mentor in the FirstRound Capital and TechStars networks as well as within his University alumni communities. Adi was born in India and immigrated to the US at age ten. He attended Princeton University (graduated with a degree in Politics) and the Stanford Graduate School of Business. He lives in the suburbs of New York City and has two adult sons and two lovable, crazy dogs.

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