There are several dimensions to your question.
Let's see if we can pull out atell them from the "giant hairball" of holding a job, ambition, and career pivots.
1. Self-identity: Where you see yourself in 3 years? How an individual answers that reveals a lot about who they are and they see themselves. In my individual and group work with executives exploring their career options, I have found extraordinary levels of myopia and limited-horizon thinking.
2. Imagination: If you were to quickly sketch an ideal working environment and career accomplishments, what would be the particulars of that desired future state? Again, I am surprised about how fuzzy and unconsidered most replies are to that question. When I dig a little deeper, inquiring as to how they feel about the future, most report being perplexed, afraid, or deeply unsettled about their future well-being. So of course when they imagine a future on that baseline emotion, they must edit heavily the products of their imagination: panic, bread, and loss of all the find dear.
3. Unfinished business: At what point in your career if you decide to play it safe, taking only easy shots on goal? This one is a lot more complex. It will reflect how good they were and the accolades that followed ead career victory. It will reflect the battles, setbacks, resentment, and regrets that they still carry with them on a day-to-day basis. Mind you, most of us carry a lot of history; we also get pretty good about ignoring the herd of elephant in our psychic rooms. Most of us have not yet conducted a thorough recapitulation of these high and low moments, identifying our God-given gifts, genius talents, core values, and optimal social contexts--mostly hidden by our resentments and regrets .
4. Different ground rules: What are the ground rules and core protocols for winning in a chaotic, fast-paced, and consequential start up and buy the what are the ground rules and core protocols for winning in a chaotic, fast-paced, consequential environment? Most corporate professionals learned that winning entails playing by the rules, the first one is that it's game and it has rules. Start ups do not have rules. Their cofounders make them up as they go along and change them on what seems to be an arbitrary basis - whatever works. For carpet professionals, this is a no-win situation.
5. Best options in the Startup Economy: Given your talents, ambitions, and social capital, what a my best options for pivoting my career into an equity-gaining situation of a startup? Well, it gets pretty interesting at this point. Most corporate professionals are not a good fit until the start up gets the size of about 50 people or more. And that could be much higher, given the culture of a particular startup. Only most good equity positions are gone by the time the startup hires its 20th person. Again in our individual and group work, we have found that corporate professionals must not only retool themselves (skills, attitudes and referenceable results), they must repackage them to meet very concrete but ubarticulated needs of start of cofounders seeking passion, cultural fit, invincible resourcefulness, and the humility of an apprentice.
I suspect there are at least four and maybe as many as seven more factors such as I ennumerated above.
There are some 15 million corporate professionals who will be forced by technology-driven circumstance to execute a career pivot, confronting the fact that their industry has been disrupted, career track truncated, few replacement-job openings for their particular talents, and global competition for the remaining jobs.
Executing a career pivot starts with the determination that you have no better option.
This embraces a core insight about human motivation: human beings will not take constructive action until the current state becomes too dangerous for inaction.
So you need not worry about your friend. It will only get worse from this point forward. He is a lobster in a slowly warming pot of water. It is not a matter of if, only a matter of when and how parboiled is willing to become!