What is the Career 3.0 Approach to the Professional Journey?

What is Career 3.0?


“I’ve learned that making a ‘living’ is not the same as making a ‘life’.” — Maya Angelou

Much of the career advice I read counsels that “the path to success” today requires building deep and specialized knowledge in a niche. And that staying focused in that niche for an extended length of time will pay dividends, eventually.

While this advice makes sense to me – people (including me) “pay” with our time, attention, and money to listen to the opinions or experience the work product of specialists and experts – I am not wired to follow that path.

Reflecting on the learnings from my career journey, I propose an alternate path to career success (extrinsic rewards) and satisfaction (intrinsic rewards). While less commonly discussed than the specialization approach, it is gaining in followers. This different approach also fits well with the secular changes happening in the world of knowledge and artisanal work.

Career 3.0 journey


I call this “Career 3.0.” This approach to the professional journey combines five elements.

  1.  Being a generalist with a breadth of knowledge and the ability to “connect the dots” (sometimes unseen) across functional areas, industries, and business models.
  2. The ability to execute (i.e., make or build things of value, get stuff done) and not just advise.
  3. Taking a portfolio approach to your career — doing multiple things simultaneously (what we call “side hustles” today) and doing different things over time.
  4. Building on your mix of unique and diverse talents, which are not often put together in a single job description.
  5. Defining “success” on your own terms.


My Professional Evolution

Career 3.0 involves being a bit of a contrarian. I have evolved to get here.

In 1990, when I applied for my first full time job after college, my expectation for work was “Career 1.1.” Knowing I was not cut out to be a doctor or professor, my view on a career in business was influenced by the “wisdom” and experiences of my parents and other relatives. I was focused on making a living. In retrospect, too much of my energy was directed there.

By 1995/1996, while studying at Stanford for my MBA, I had changed my perspective to Career 2.0 – wanting to work for companies disrupting the status quo with technology and getting some equity. This choice still optimized for making a living, although there was more of a “mission” and “passion” element to it. I got lucky and participate in the wireless industry when it was considered a toy for the very rich.

Over time, as I gained experience, I moved “up the corporate ladder,” thereby increasing both my cash and equity compensation. I moved amongst start-ups and kept hoping that one of them would have a successful exit.

I knew I did not have the educational skills or the practical work experience to be a technical co-founder. Nor did I have the disposition to be the CEO/founder. So, I spent much of my professional journey to date in different versions of Career 2.0.

I left full-time W-2 employment in April 2019, not of my own choosing. Today, I am glad that I was forced to reckon with this change. I am embracing Career 3.0. I see myself as both a “creator” and an “advisor.” These terms are my versions of what Paul Graham described as the “maker” mentality in his seminal 2009 piece, “Maker’s Schedule, Manager’s Schedule.” I have transitioned from a senior leader in a W-2 role to something different and which I find far more appealing (at least for now.)

Why was I able to make the change? Multiple reasons.

1. Good Fortune / Ability to Accept More Risk.

Today, I can “afford” to change my perspective. While not exceptionally wealthy, I have had career success and am comfortable. I know I can make a decent living in a Career 3.0 format.

Using the graph below to illustrate a point, I see Career 1.1 as embracing the 20% risk level, Career 2.0 as taking the 50% risk level and Career 2.1 as the 90% risk level. As one moves up the risk-taking curve, the median expected return (middle red dot) is higher. So is the dispersion of potential outcomes. Those in business, tend to pick career patterns based on different risk preferences and appetites.

Risk Levels Career 3.0


I don’t have an effective way to plot Career 3.0 on this graph. My beliefs are as follows:

The median expected return will be materially below Career 2.1 as will the level of risk.

Career 3.0 offers people who share certain values a lot of additional return that is hard to convert into a monetary equivalent. These returns are captured in thing such as greater autonomy, purpose, variety, learning and the like – all things that I attribute a lot of value to.

2. Structural Social & Cultural Change

I would describe the years 1930 – 1980 as largely embracing a “Collectivist” approach to work / career. Employees were part of a “family” and gave up some upside in exchange for less risk and downside protection (loyalty from the company.)

The last 50 years, since the Thatcher / Reagan elections, have brought a sharp and steady swing back to an “Individualist” ethic around work and career. This includes more personal independence and choice as well as much more opportunity for upside offset by a lower safety net (less employer loyalty and protections for employees.)

Social changes have demanded that people embrace more career risk and thus the need to find opportunities for higher returns. Hence the transition from being wedded to one company to the norm now being short stints (2-5 years) at multiple start-ups trying to find one or more good equity outcomes.

3. Professional Journeys Are Longer.

The combination of extended life expectancy coupled with better health (physical and mental) later in life is a meaningful contribution to people “working” for more years.

The desire for continued intellectual stimulation coupled with leveraging our talents to keep contributing to society are also driving a longer commitment to career and work.

Yet the workplace has not adjusted to bringing and keeping older employees (especially 45+) in interesting mid-level roles. Once we’ve celebrated our 50th birthday, the world of knowledge work expects us to either be at the top of our function, or to be doing something else. Another reason for the appeal of Career 3.0

How is “Career 3.0” more than being an Investor?

If we scroll Twitter or follow the business press, we see multiple daily announcements about new “venture funds” or other “financial capital vehicles” being started by groups of former operators.

My definition of Career 3.0 includes being a creator who builds something and gets their hands dirty. You may add elements to your portfolio of work that involves being an advisor. However, the core of the Career 3.0 value add to the world is determined by bringing your expertise and execution / making skills to bear.

Career 3.0 is Not for Everyone.

Embracing a “portfolio of work” is not for everyone. It is rarely where one starts the professional journey. Each of us needs to find the risk/return in the professional journey that suits our values, lifestyle, and other priorities.

However, as you we mature through our professional lives, I would encourage everyone to consider a Career 3.0 path.

My Advice for those earlier in their Professional Journeys.

I have one son in the workplace (18 months post college) and a second almost done with his bachelor’s degree and thinking actively about “paying work.” I am approaching this post with the thought of what would I tell them if they choose to ask my counsel, which, as any of you with children knows is unlikely.

1. It is a Long and Winding Road. Enjoy the Journey.

The destination is not obvious. There are a lucky few (the extreme minority) who know what they want in their late teens and early twenties, make it happen and remain engaged in that field for decades.

Embrace the uncertainty. Be prepared to change your focus, function, and role. Many of the jobs you will hold in the future may not be widely known today or be enabled by technologies still to be commercialized.

Part of the joy of the journey is knowing what you stand for (i.e., values and priorities) and finding different ways to express those values in the world through “work.”

No one can really predict the future. Listen to those who tell you about a specific path to a particular destination with skepticism. Take in their advice and remember if it were easy enough to boil into a formula that applied to lots of people, there would be more success and satisfaction in the world.

There will be challenges along the journey. Reframe the challenges as opportunities.

2. Build a Portfolio of Skills. Be Curious. Keep Learning. Try New Things.

Careers of the past were mostly about doing one thing really, really well. I still hear that advice being offered in the form of “become an expert in a niche.” This is the path embraced by academics, specialist doctors, lawyers and various other professional services providers who specialize in a niche. While I know forecasting the future is a fool’s errand, my gut tells me that technology will increasingly replace human expertise which is focused on going deep in a single niche. Human skills will be more valuable in being creative, by connecting things that are not obvious but related, in doing things that are novel (creative) at least for the business they are applied to.

Building a portfolio of skills means taking time away from specialization in your function (whether engineering, marketing, people operations or finance) to learn about what others do in their roles. I would approach these dialogues by asking about what problems these other functions are solving in their jobs, as well as how the solutions impact the customer and the business. Try to figure out how they approach problem solving – it will be a different approach than yours and broaden your skills.

Also, try new things. Ask for and accept new projects or roles, especially those which make you feel a little uncomfortable. Look to work with superiors who are ok with failure (we all fail) and are committed to teaching and developing people.

3. “Rewarding” Jobs will combine a “Creator” and “Advisor” component.

Further drawing on Paul Graham’s essay which explains why “makers” are different from “managers”, I agree it is critically important to retain some “creative” skills as we move forward in a career. The most obvious such skill is programming, but it can also be writing (or other media creation), or teaching (or other performance) amongst other items.

The traditional career path in companies is to go from being an individual contributor to a manager to a “manager of managers.” That is the accepted route to greater compensation as well as increased status and respect. However, it is also the path which is most likely to make you redundant when bad things happen. If you are faced with a downsizing and are forced out of a mid to senior management role, it can be awfully hard to find the next role, especially if you are over 50.

Try to always keep some familiarity with the creative part of the job. While it will not be the most efficient thing to do, it is a worthwhile insurance policy you are buying, even if you plan to stay in corporate America (by which I mean large technology companies) all your career.

4. Remember the Eulogy Virtues.

David Brooks talks about the differences between resume virtues and eulogy virtues in this short TED Talk he gave in 2014. In career advice, we are counseled to focus on and talk about resume virtues – the skills we have, the work accomplishments (expressed numerically and specifically), and what we have created. We know that our LinkedIn profiles and interviews are evaluated by AI, so it seems reasonable to focus on the resume virtues and optimize how we present them.

My perspective is that professional journeys are still and will always be built through some serendipity and a lot of personal relationships. Make the effort to help others just because, give away your time (albeit not to the point of exhaustion.) Embrace a positive sum view of the world. Even if your one piece of action will not by itself change the world, make the effort to do what you can to have a positive impact on others and the world.

People will remember you for that. The human connections you make and the gifts you give away will come back to you in some way in the future. And, you will feel better about yourself along the journey.

The Core of Career 3.0: Define “Success” For Yourself.

When we meet new people, we will most likely ask each other (especially if two men are involved), “What do you do?” It is our way of evaluating where we fit in relationship to other and what are the points of similarity or difference. That question is a shorthand for evaluating “success.” The metrics for success have been determined and agreed to by society and are based on achievements that can be measured by others (i.e., wealth, titles, degrees etc.)

Switching into a Career 3.0 mindset is about defining “success” for yourself. Regularly ask yourself, “What do I want to achieve and feel in this part of my professional journey?” Monetary success and a comfortable, enjoyable life are often part of the outcome you are seeking. But they may not be the only metric that matters or the most important metric.

Don’t let others – family, friends, society, pundits in the media – define your path. Listen to the advice of others with an open mind. And then, follow your heart.

Define your own path and your markers for success. It is hard to do and will be worth it.

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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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