The entrepreneurship craze is over. Now what?

You can easily trick yourself into believing that entrepreneurship is all the rage among young people. Hacker meet-ups, entrepreneurship clubs on college campuses, and the sudden growth of incubators and accelerator programs can present fodder for this case. But these are really just ways to talk about starting a company.

Zachary Slayback says, “Entrepreneurship among young people is actually relatively uncommon. Relatively few young people today own stock in a private company, and a good chunk of those who do likely aren’t entrepreneurs anyway, but rather work for companies who issue equity to their employees.”

The reason entrepreneurship is relatively uncommon is it’s too high risk for 90% of Generation Y. They are simply not risk takers. Their parents raised them to be successful in the most common sense of the word, which precludes risk taking. Because risk takers look crazy, not successful. Confirming that reason is the Wall St. Journal, reporting that Gen Y is starting businesses at a much lower rate than Gen X.

Gen Y wants fulfilling work, but starting a company is not-fulfilling, it’s all-consuming. There is no half-time alternative. (The difference between an entrepreneur and a startup founder is not the hours or the pressure or the craziness. It’s the size of the business.)

The picture up top is what people want: stable, but interesting home life. The problem is how to get interesting and stable at the same time. Here are some answers.

Recognize that your job is not your life.

Another way to look at it: your job is not your life, so a super-interesting job does not make an interesting life. It makes a workaholic. Think about it: anyone you know with a status symbol job is someone who works all the time or took enormous risks instead of picking a predictable path.

After coaching hundreds of people I’ve discovered that most people who say they are in unfulfilling careers are actually unfulfilled in their personal life. This is because work is not your life, it’s your work, so if you’re unsatisfied in your life it’s probably not a problem with work. It’s just much easier to ask for career advice than life advice. And it’s much easier to change jobs than change your personal life (get married, have kids, stop being a slave to your parents’ vision for your life, etc).

The good news is that we can stop listening to the hype about how entrepreneurship leads to fulfillment. We know it’s not true.

Get a safe job.

Dan Lyons author of Disrupted: My Misadventure in the Start-up Bubble, spends 300 pages talking about how poorly startup employees are treated. And those lucky employees who do make a ton of money from working at a startup are more like lottery winners than people who do something significant in their job. So don’t bother with the startup.

When you work at a large, stable company you get a regular paycheck, predictable systems, and a management team that answers to a board of directors. There is a career path for you at a company like this, and it is safe and predictable.

Which means that you can create the life you want outside of work. You can make a safe, stable family, and you can follow your passion—which is not something you should get paid for, but it is something you should make time for in your life.

Climb a corporate ladder halfway.

I recently talked with the bestselling author in India, Karan Bajaj. And I realized he has created a lot of ways to make a stable, boring job a path to personal passion.  He worked at Proctor and Gamble and wrote his first book at night, after work. You can only do this if you actually have time after work, if you can keep your work from seeping into all hours of your day. And the best way to do this is at a corporate job.

Take sabbaticals.

Taking a year off in between jobs is an effective tactic for completing projects that have a clear start and finish, but it won’t help you balance kids and work. It’s really hard to take vacation time because the 24/7 nature of technology means we often work when we are not supposed to be working. But if you take a year off, you are totally removed from work. Karan wrote this most recent book, The Yoga of Max’s Discontent, during a year-long sabbatical from work.


Not everyone fits into a large company, and not everyone feels comfortable with a boss. If you think you’ll die going into work every day, then freelance.

Freelancing as an alternative to a daily grind. Freelancing is not entrepreneurship. Freelancing is finding someone to work for, but you work for them occasionally rather than every day. Just like getting a safe job, someone else has the company vision and you fit yourself into it.

As the entrepreneurship craze declines, freelancing rises, and by 2020 40% of the workforce will be freelance.

Freelancing is great if you want control over your work hours without the craziness of entrepreneurship. So it makes sense that one third of freelancers say they do it for their kids. (Here’s how people get the guts to start freelancing.)

Work in slow motion.

I think this is the route I’m taking. Because I told Karan I’d be writing about his book on my blog. And then it took me one month to actually publish the post. This tactic doesn’t work for building anything, but if you already have what you want, working in slow motion is a way to preserve it without destroying your personal life.

Did you see the movie Zootopia? The sloth? That’s what I feel like when I’m working. I used to criticize myself for working so slowly, but I am coming to terms with this pace. It’s like people dialing down their corporate jobs for children. Or taking a sabbatical to write a book.

I’ve had the photo up top for a long time, but I didn’t use it because I felt like it’s too domestic. But now that I understand my personal life better, I see the cabinet full of dishes can be interesting in the right light.

Most people are not balancing work and kids so much as calibrating between stability and instability. We each look for a way to create a stable enough life so we can enjoy what is interesting about that life. But not so stable that the thrill is gone. The art of life is in the instability. But no one enjoys art if they can’t eat.

38 replies
  1. Amy Patrick
    Amy Patrick says:

    What a great article! One group you didn’t hit upon which seems rampant in my industry (textiles/bedding) and NYC: onsite freelancers. Low pay, no benefits, and onsite. Wheee.

  2. Jenna Anon
    Jenna Anon says:

    I recently returned to work after a 1 year maternity leave (not in the US, obviously), and returned to my stable job at a large corporation… I still enjoy my job, but I am also enjoying my life, and I am making sure I keep boundaries (I am the tail end of gen X, almost gen Y). The only thing I regret now is not job hunting towards the end of my leave to check market value for my work/industry and in case there was an opportunity to jump for more pay. But I didn’t, and my industry and city hits a summer slump, better to look in the fall.

    What is your opinion on people calling themselves entrepreneurs who are actually just suckers in this latest incarnation of pyramid schemes, I’m sorry “direct marketing”/”network sales” ? Seems to be hitting a lot of gen Y who are looking for more home life and a non -corporate job.

    • Cherie Noel
      Cherie Noel says:

      I bet the answer is residual income, it is a wonderful thing. And by the way, not all network marketing companies are bad, that is why there are so many people young and older, educated people starting their own businesses and yes it is our own business and for some we do it part time when it fits our schedule. I would love to show you how mine works so you know they are not all “bad”.

  3. Pirate Jo
    Pirate Jo says:

    The biggest employer in my area (think of a bank with a stagecoach and horses as its corporate symbol) has been laying off full-time employees, but slowly and quietly, so as not to alert the local press. I swear, when this company goes full-throttle on layoffs, the entire city goes into a tizzy! But it isn’t that they aren’t hiring people. In fact, here and there they ARE hiring full-time employees, but most departments/divisions are under the stipulation that only contractors can be hired.

    If you do freelance work, this is a gold mine. You have no trouble finding work. Plus, this company will hire no contractor longer than 18 months at a time, and won’t take you back for six months, so you are guaranteed a 6-month sabbatical at the end of it.

    The downside is, you have to get your own health insurance. I’m 46 and have a high-deductible policy that still costs me $206 per month just to have – no dental. But you can put enough money into a Health Savings Account to cover the deductible (I think mine is $6,500) tax-free. And that’s the money I use when I go to the dentist and spend $170 getting my teeth cleaned. Just make sure you stick a few hundred in there every year.

    This set-up works great for me. If anything, I am fending off my staffing agency because they always want to stick me in new positions when I don’t want them. After working for a year or 18 months, I want at LEAST three months off – six is better.

    You have to do things differently than what you were told. For example, you don’t roll around with a giant mortgage balance and a big house payment. You pay off your house and keep your previous (paid off) home as an investment property, which makes up for the fact that you get no 401K match. You keep a lot more cash in checking and savings. Living paycheck to paycheck? No way, you keep TWO YEARS worth of money around that you can get your hands on, just in case your local economy takes another hit and a big round of layoffs ensues. You don’t want to be stuck with only three months’ worth of living expenses in the bank when it takes six months to find another job.

    But as I said earlier, it’s easy to find work when you’re freelance. Companies don’t have to pay for benefits, and when they decide they don’t need you anymore (or when their department budget runs out of money), they can just let you go without having to worry about paying higher unemployment insurance premiums to the state.

    • Amy Patrick
      Amy Patrick says:

      Wow. I am freelancing in the wrong industry. My industry (fashion/textiles/bedding) tends to hire freelancers only when needed, then tell you when you are not needed without a lot of notice. Low pay, no contracts, no sabbaticals. :/

  4. Laura
    Laura says:

    Why am I not watching you give this as a speech at the PAC in Appleton? It’s so good. If not a live event, how about a podcast for all of my stressed out friends and their college age kids? Such a simple idea, but a complete disruption of life as we’ve come to expect it. This INFJ says BRAVO.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks! I’ve been thinking about these ideas for so long that sometimes I forget if they are new or not. Your comment makes me happy.


  5. Lucy Chen
    Lucy Chen says:

    I can say from personal experience, that what you say here about not finding the work/job satisfying has more to do with an unsatisfying personal life, partner, parents, etc., or our own spiritual state.

  6. Rebecca Stafford
    Rebecca Stafford says:

    Love how you are coming to terms with your ‘slow’ pace.
    You know what they say about slow and steady – avoids burnout and works effectively (i.e. works on the things that actually matter, rather than majoring in minor things).
    And it is a truly lovely metaphor, I mean photo.

  7. Stephanie
    Stephanie says:

    The sabbatical idea makes a lot of sense (and coincidentally I’m on a short sabbatical before moving to the other side of the world next month). By removing ourselves from the daily grind we give ourselves enough headspace to work on whatever that fulfills us.

    But I wonder if the example of Karan Bajaj can be applied to most other situations. After all he has an impeccable profile and is well-established in his specialty as a marketer, so he doesn’t have to worry about being replaced. For most people who want to stay employable after their sabbaticals they will need to think about how their side project melds with their own career story so that it will appeal to potential employers.

    • Penelope Trunk
      Penelope Trunk says:

      It’s a good question, Stephanie. From what I’ve seen, a sabbatical has the same impact on your career that maternity leave does. That is: You can certainly re-enter the workforce where you left off. But it’s hard to continue to move upward because people don’t think you are that serious about your work.

      And I think this happened to Karan as well: he left Proctor and Gamble after the sabbatical.


  8. Wayne
    Wayne says:

    Gen-Y or not, I think there’s a lot of truths in this. It really struck a cord with me partway through my own professional life. Having ventured down both roads of employment and entrepreneurship, there’s so much truth in your words. A job isn’t your life and unfortunately with entrepreneurship, it is.

    I’ve considered going back into regular employment just so I know when a job “turns off” and I can get away from the work. I worry, though, in higher-paying jobs that it can be just the same.

  9. Jim Grey
    Jim Grey says:

    I think that the big-corp jobs will not be a great fit for the young generation either. They tend to be control environments, very top down, where compliance is praised.

    I’m telling my sons to shy away from big corp jobs and look for the mid-sized company instead. They’ll get most of the stability and, usually, a whole lot less of the stultifying top-down rules.

  10. Scott Asai
    Scott Asai says:

    Really insightful article Penelope! I always thought Millennials were more risk takers vs. risk adverse. Makes sense to protect lifestyle thought. I do think that’s the new trend (over following your passions). I definitely shared this with friends!

  11. Jack
    Jack says:

    Spot on, especially for life here in Silicon Valley. It’s called the IPO lottery for a reason.

    The other unspoken truth in tech is age discrimination. Try finding an interesting, well paid job here after you hit 50 – it’s a painful slog. Having converted to your freelance passion by then will give you much more freedom, satisfaction, and security.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks for pointing that out, Jack. I don’t think people realize that in Silicon Valley/San Francisco if you are 30 and you don’t have a prize under your belt already, then you are old. There is very little room for personal exploration in these areas because age discrimination sets in so fast for people who are not at the top of their game by 30.


  12. Leslie
    Leslie says:

    As usual this is a great article, however freelancers do have much in common with a traditional business. As a freelancer you do have to pay estimated quarterly taxes as well as the employer portion of social security in addition to the employee portion. You also have to stay current in your field to keep getting work but you pay for the training instead of a corporation. One of the advantages of working for a corporation is getting trained and having upgraded computers at their expense. The good news is, as a freelancer, you can write off most of these expenses. My experience is that corporations who hire freelancers want to make sure they are not fined for having an employee without paying the requisite FICA taxes so they want freelancers to have filed for a DBA and have a separate bank account, in addition to a website and or course, more than one client. Many independent contractors are really employees as they do not have the ability to set their own hours and are required to work on site at a particular business. There is a great book on this topic called “Small Time Operator: How to Start Your Own Business, Keep Your Books, Pay Your Taxes, and Stay Out of Trouble…” written by a CPA

  13. Ian Boreham
    Ian Boreham says:

    You seem to give the impression that work and an ‘interesting life’ are more often than not different things? Writing a book must be interesting but going to work must not be? If this is the case then all it really means is that people have aligned their careers to their interests and values poorly. Those people that have aligned themselves well are ‘workaholics’ and supposedly missing out on the more interesting things in life? Interesting when we assume that our lives must be what everypone else is striving for.

    • Penelope Trunk
      Penelope Trunk says:

      What I mean is that people who find their work interesting and fulfilling do their work all the time. Because why wouldn’t they? It’s fulfilling.

      Most people are not like that. Most people cannot find fulfillment in work because people only make money doing things most people don’t like doing — putting money ahead of people, taking huge financial risk, going to meetings all day, etc.

      The idea that work can be fulfilling for most people is inane: we don’t pay people to do things most people would find fulfilling. We expect people to do those things for free.


      • Ian Boreham
        Ian Boreham says:

        I totally respect your point and don’t disagree that it seems to be the reality for most people but I just can’t accept that work cannot be fulfilling for a lot of people. It seems sort of defeatist to me and immediately raises the question as to why this is the case. The reason you give…’most people only make money doing things most people don’t like’ also seems a little bit like a cop out without much thought behind it. I think the issue is much deeper and probably sits somewhere between ..’people are getting worse at figuring out how to be happy’ and ‘larger companies could do a much better job at improving how they interact with employees’.
        The interesting challenge for me is to help people find happiness in work that you potentially view as boring. I see this as a more realistic and useful approach than selling some sort of ‘it’s inevitable to be bored at work so write a book’ approach ;)
        ps strictly business – love your work. :)

        • Blandy
          Blandy says:

          I had a corporate job. I enjoyed the work (competitive intelligence and organizational change) but after too many projects were either tossed in the trash or ignored, I left. Why was I wasting my good time on work that never accomplished anything? My ego got tired of it.

  14. Lisa
    Lisa says:

    This is so perfect. I’m looking for work and really focusing on mid-level because I don’t want to give my whole life to a company – been there, done that. It’s taking forever, and I’m freelance writing in between, but that’s not a living! I’m also an INTJ but I think maybe I’m not an INTJ, and I just think I”m an INTJ.

  15. Natalia
    Natalia says:

    This is the best article I’ve read on the subject, with a very clear perspective. I hope more people have a chance to read it. Thanks.

  16. Mariana
    Mariana says:

    Congratulations Penelope, I think you went ‘full circle’ now. I found a mentor at my job and she has been saying things like this, but it took me a while ‘not to resist’ to what she was trying to teach me. Truth is not what we want to hear most of the time…Tks for your writing!

  17. John
    John says:

    I’m not surprise about the Gen Y situation. Up until 3 years ago, I had a corporate position that involved hiring and managing entry level professional positions. Starting about 8 years, all of my new hire were Gen Y.

    It was a different attitude towards careers. None of them were overly interest big promotions. They wanted to do their 40 – 45 hours. I remember telling them that they would need to leave the company if they wanted a big pay increase.

    They did not want to leave. They would have been happy with small promotions. They were fine with doing crappier work if they felt that it had some value and if they felt that management team was competent and had game plan. The job was just how they made money for their life.

    I think that many large organizations could go back to the old HR job structures that had numerous levels for job (e.g. Analyst, Analyst II, Analyst III). They would have been thrilled with a small promotion and small pay increase every other year.

  18. Jennifer
    Jennifer says:

    Monday, April 18th. Normal, busy day. Too busy to check my personal messages and eat at my desk. Discover Monday night that my friend had sent a message wanting to do lunch. Reschedule for the next week.
    Sunday, April 24th my friend took her own life. I’ll never have lunch with her again. If only I hadn’t missed her message because I was busy.

  19. Karelys
    Karelys says:

    I stumbled upon this sort of by chance, sort by being a typical introspective person.

    I have a job I love and doesn’t pay much.

    But I tell myself that the money I’d need to have the life I want would require a lot lot lot more money than what my job pays. So I think of the things I want. I think of the days that I am the happiest. I am always astounded how little money that took.

    Money is there one way or another. For an INFJ like me, copious amounts of time to think and be alone and process life is necessary.

    I have that.
    I dance every week.
    I have a bonfire four days out of the week with my kids.
    I see my family most days of the week.
    I spend big blocks of time with friends having soul nurturing conversations about spirituality, love, career, art, politics, etc. every week.
    We hike.
    We drink wine.
    And eat a whole loaf of rosemary bread with brie at the peak of the hike at the winery.

    I want more, like all humans.
    But I tell myself that I’ll find more later, when it comes from a place of abundance.

    I am healthier than I’ve been in a long time. Thanks to all the time.

    So it was money or time.

    I earn little money but I have significant time available. To sleep. To live.

    So for now it’s the right place to be.

    Even if I am putting like $25 in savings every month. I am forcing myself to save even when it seems puny. It’s better than nothing.

    It’s my birthday at the end of the month.

    I’ll fly a plane just because I want to.

  20. Brittany
    Brittany says:

    I enjoyed this read. However I have a question of what exactly qualifies a job as “safe”? My dad got laid off after being a faithful employee and working his way up within a company for twenty years, thinking he would retire there. He missed a lot of opportunities to start his businesses and sometimes even told others his ideas just so he could see them become a reality, and some did and they were successful. In a way his job worked out because it at least provided for us while we were young, but what if he could have done more through his own company? Penelope how would you qualify a job as being safe?

    • Karelys
      Karelys says:

      I wonder about this and the thing is, at a certain point you have to decide for safe enough right?
      The latest post is about Cheryl Sandberg leaning in.
      There’s no foolproof deathproof way.

      Your dad’s choice worked out because the job ended once you guys were older. Neither self employment nor corporate job will ensure that you’ll have income at all times while also having time to live life.

      I think the jobs are safe enough according to your situation. Life is always unexpected.

  21. Meghan
    Meghan says:

    This post resonates so much with me. My SO, several years older than me, is an entrepreneur (CEO of a company with 70 employees in 2 years) and is very close to complete burnout. He had a huge amount of energy and drive when he started but running a growing business, with more and more people depending on you all the time, takes such a toll and you can’t ever press “pause” on the responsibility. He has recently started wistfully talking about how nice it would be to get a regular job and take home a paycheck. Plans are in the works for him to transition out of the role but he has to hang on for a while longer.

  22. Marshall
    Marshall says:

    Taking time off has struck a very real chord with me. I did it (am still doing it) and have started my own business adventure at my own pace. Left the corporate world to build furniture in my small shop.

    Keep it up!

  23. Dr. Alzabith
    Dr. Alzabith says:

    Very interesting article and good information, but i think entrepreneurship is the ultimate solutions, its true that entrepreneurship is not common in youth because it required to of potential and wait. but ultimately it wins i think so

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