Are you selling your entrepreneurial soul if you take a day job?

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I was really excited to do this interview with Andy Wibbels of after I heard that he took a "day job" as Marketing Manager at Six Apart.

I have known Andy for a long time and have always admired his candor, sass and brand, as well as his business sense.  Since he has done almost everything right to create an effective business, like:


  1. Create a successful blog
  2. Define and own a particular niche
  3. Develop a huge mailing list of devoted followers
  4. Team up with great partners like Darren Rowse and Michael Port
  5. Write a successful book (Blogwild)
  6. Get mainstream press like the Wall St. Journal and USA Today

I wondered what would make him decide to become an employee.

I think his answers will interest you, if not challenge some of your long-held beliefs about entrepreneurship.

Check out the podcast interview here.  It is about 36 minutes.

My conclusion at the end of the conversation is that there is no work configuration that is inherently evil.  It is all about what you are looking for, what is important to you, what you are willing to trade off, and how likely you are to be successful on the "outside."

As for me, I think I am, as Jim Collins once said about entrepreneurs, "constitutionally unemployable," but that doesn’t mean I don’t respect someone’s decision to take a day job.

What do you think?

Funny backstory:  You will hear as I introduced Andy that I said that Six Apart made Wordpress and Typepad.  As soon as I said it Andy caught me.  The funny thing is that Andy and I (as well as others at Six Apart) have been going back and forth about Wordpress vs. Moveable Type for my blog redesign.

Sorry for the Freudian slip Andy!  🙂

14 Responses to “Are you selling your entrepreneurial soul if you take a day job?”

  1. This is a great topic for discussion. Very often when I coach people around this subject, unfortunately there is a sense of shame if revenue needs dictate that getting the dreaded J-O-B is neccessary. I say, do what you need to do, but create a plan. Many people want to start small businesses but don’t have enough financial reserves to fall back on. Or they have a business established, but get desperate, and like the sleezy guy in the bar trying to pick the gals before closing time…no one is attracted to desperation! So if you CHOOSE to take a job, maybe it could be part time while you are continuing to grow your biz. Just make sure it’s in alignment with your values.

    Just my two cents!

    Take care,
    Therese Skelly

  2. Great podcast Pam and Andy!

    I’m torn about his decision because if anyone would have success and not need to return to a day job it would be someone like Andy. This makes me lose heart in my own pursuits. He is right though, running a small business is hard.

    But, I think that an entrepreneur sees the bigger picture and a new role, no matter where, is always a stepping stone to something else.

    However, if I totally understand Andy’s acceptance of a position at Six Apart. I have met the CEOs and I use Movable Type since 2005. Great company, great folks, great vision. What’s not love. I’d go too! He will be on the cusp for sure. That’s super exciting.

    And Pam, Wordpress?? Shame on you =)

  3. Hi Pam:
    It’s a tough decision. If you are a successful entrepreneur I can’t find many reasons why somebody may want to get a job. The only way I would do it if I were in that position is if the job would offer me the chance to learn something new that fit into my long term goals, if I could get all the flexibility I wanted (autonomy, time-off when needed, etc.) and if my business had the processes and systems in place to keep running without me for a while.

  4. Richard says:

    I say do what you gotta do! I mostly agree with Andy’s podcast. If you can find a full time position which complements your business than go for it. I think his situation is an exception and not the norm. For the rest of us I’ve found it difficult to start a business and hold down a corporate job. Thats why I’m looking to buy a busines vs. starting one from scratch. The cube life sucks too much of your life energy from you. It’s kind-of like that Austin Powers movie where they steal his mo-jo!!

  5. Shama Hyder says:

    I say “whatever floats your boat!”

    Time really dictates work choices. Some times in life, a job works just perfectly. Other times, you really want to venture out on your own.

    -Shama Hyder

  6. It has long been my goal to learn to grow my blogging/e-publishing business into a full-time income. Over the years, I have resented the energy I must put into my “day job,” but I have to admit that the skills I picked up on my own together with the ones I’ve learned in my day jobs, have helped me be more successful in both situations. My two roles have actually fed off of one another. I’ve learned some great things about business in my jobs, and I’ve brought some valuable skills from my blogging, Internet marketing, etc. that increase my value at work.

    I’d still rather be on my own, and I believe I will get there, but I’m learning things at my job that I’ll need. I also have fewer illusions now about how difficult self-employment will be, and what it will require of me.

    Learning to use my ever-changing situation to my greatest advantage has helped me keep a productive perspective.


  7. Cora says:

    I started as a part time entrepreneur, but I found that when I started working for myself full time, the ROI was worth it. Since I had more time to invest in my own business, business was growing and now I am completely self supporting. No need (or wish) to go back to a boss.

  8. Peter says:

    Congratulations on an excellent podcast!

    I’m really glad you pointed out that working for “The Man” can be a positive choice. That’s an important message for people like me.

    I’m picking myself up and getting a career started after a long spell of illness. I know I’m not ready to go it alone, but I see no reason not to apply entrepreneurial thinking to my career. I can think of my career as if it was a business, right?

  9. Dan Clark says:

    I think this is a very important discussion.

    I liked the fact that you both agreed and made clear:
    1.Small business is hard.
    2.The nature of your employment does not have to be binary.
    3.Just as you encourage people to start their own business it doesn;t mean you can’t go back to an 8-5

  10. Interesting post… have you read Daniel Pink’s “Johnny Bunko”?

    I would suggest that he would have a different vantage point. Or perhaps it is just me.


  11. Woops, paste error. Meant to say “you just have to build your assets and never stay in one job too long”

  12. Working for the man is fine as long as you’re building equity in yourself outside of your day job.

    This means blogging about your field, making friends on social networks, and meeting people that you *don’t* already work with.

    Remember, any company has to please shareholders and protect the organization first. HR departments are not there to help you but to protect the company and to put protocols in place so you can’t advance too far, too fast.

    Job security is an illusion. Companies merge or downsize. The boss that has your back will leave. Cultures change.

    You can make great friends with colleagues, but the organization itself is not a person. It doesn’t love you. It can’t.

    Of course many jobs are fulfilling and doing fulfilling work with good people is one of life’s great joys, you just have to, and never stay in one job too long:

    Wow, that was a bit ranty 🙂 Anyway, great podcast and congrats on the job Andy. Working at SixApart sounds like a lot of fun.

  13. I was once asked in an interview (by the CEO, so I knew I was on the short list!) whether I thought that I could handle the structure of a corporate environment, as he pegged me as a “creative type.” The honest answer I gave him was that I chase “interesting work.”

    There’s the rub. For example, I went to school with a lot of smart engineering types. Some of them have made a living at one time or another doing tech support for home-based business people. Day to day, that work can be both rudimentary and repetitive. It might be worth taking a job at Google for a year or two to stretch the brain working on “the cloud.”

  14. Lynne Gillis says:

    OMG! This could not have come at a more perfect time. I just signed a freelance retainer agreement (almost like going back to corporate) at a marketing firm because not having a consistent paycheck was making me absolutely crazy. I’m an interior designer (that’s my entrepreneurial thing), and the market now is tough… so I felt that to save my sanity, I’d need to do something like this for at least the short term. Thanks for sharing this!