
Love Dilbert!
[This is part of the Escaping the 9-5: My Road to ProBlogging series.]
It might be a bit odd to believe that someone who loves setting off on their own and working for themselves might actually have a few tidbits of regret leaving the environment that kept him prisoner for so long.
Perhaps it’s because of all the challenges that a inevitably arise from working for yourself and having to manages those difficulties instead of someone else.
Or perhaps it’s the “guaranteed” bi-weekly check that appears in your checking account that keeps you comfortable and anxious-free at night? Sure, nothing’s completely guaranteed but some circumstances are a bit more consistent than others!
I love where I am and the people I now get to spend the vast majority of my time with but I would be lying if I were to tell you that it’s all “fun and games” and I don’t have doubts every so often.
As a result, I think it’s a good thing that I share some of the things that I genuinely miss from the corporate lifestyle and cubicle, just so that you have some more food for thought as you consider making a leap into ProBlogging!
1. Non Virtual Environment
One of the things that I have enjoyed is the complete freedom to work from home and anywhere I please at any given moment. I don’t like being told what to do and especially the way that I should or should not work!
But during the tough times of doing business or writing I can miss the consistent source of physical community, especially since my startup teams don’t have a real office (yet).
I sometimes miss the ability to get out of my seat, walk over to the next cube (we’re talking 2 feet away, at the most) and whining to my colleague about how the legal department is taking foooooooooooooooooorever to get approval for a last-minute marketing copy change for our new product.
Ah. I miss that. Throw in some nerdtalk about how last night’s epic 25-man Raid of Naxxramas went (and what loot dropped) and you’ve got a fine personal watercooler!

2. Corporate Hiearchy
This might sound a bit odd as well but there’s something powerful about hiearchy and corporate structure, insofar as it’s ability to help levelset expectations and to clarify roles.
I also hate it at the same time (and it’s partly why I left) but at times it’s a necessary challenge that, for some people, is the only way that they can work.
I understand the corporate dynamics that take place in the workplace and it’s many drawbacks – but I’m also familiar enough with how it can, when done well, improve productivity, provide foundational expectations and understanding about roles and responsibility, and how it can destroy decision gridlock when leveraged appropriately and wisely.
Some people thrive in absolute chaos – but I’m not that type of person. I still need a bit of structure within which to play with so I can maximize my core strengths as a person.
And when you’re a ProBlogger you make all these yourself and sometimes you’re everything (and nothing) all at the same time. That can be a challenge for sure!
3. Competition
You might not have ever thought about it in this way but the corporate culture and office lifestyle has competition flowing through it’s veins – and for the competitive person (like me) this is a constant adrenaline rush.
Many people are looking for the next challenge, the next step to develop your career. When managed wisely and well this is a good and healthy thing!
But when you’re a ProBlogger it can be difficult to really understand who you’re competition really is – and having yourself be your only competitor can get really boring really fast!
For those that especially thrive in cultures and environments where a competitive spirit is rewarded and thought of highly working for yourself can be a challenge at times.
What I’ve had to do is to create a lot of alternative metrics and standards of comparison so I can keep the competitive spirit alive and well, for my sake and yours!
What about you? Have you made the jump out of corporate only to realize much of what you miss? What are they?
[This is part of the Escaping the 9-5: My Road to ProBlogging series.]






I spend a decent amount of time on client sites, which gives me that jolt of reality about ever wanting to be back in typical “corporate culture.”
However, I think you hit the big one–community! We all need community, whether it’s work, family, or church we need to have a community.
My pastor gave a great analogy last Sunday:
He grew up on a farm and had to “look after the cows.” One day he asked his Dad, “What am I looking for?” His Dad simply replied, “The ones off by themselves…they’re the ones in trouble.”
Thanks for the post and all you do–it’s great stuff!
sure thing bill! thanks for being a part of this community!
I have the pleasure of being a self-employed individual working from home, and there are great things about it. Wouldn’t trade it for the world. But here’s what I miss:
1. The ability to “go home”
I worked as a desk clerk at a hotel in college. When I clocked out, I was done. I never really thought about work when I wasn’t there.
2. The ability to “go to work”
This is tough with a wife and two kids at home. It’s been a hurdle we’ve had to jump over to make sure that everyone understood that I had times when I was working, even though I was just in the other room. The requests would come for me to help change this diaper or watch the kids while my wife ran to the store. It was always “just for a minute” but it really was a stressor not only on the business but also on our relationship. We’re approaching the point now where we treat it as if I’m at an office a half-hour away.
Those are fantastic points, Loren.
Those are some of the biggest struggles for me as well. When does the work day “end” (answer: never) and when does home life get “cut off” from work life (also never). It makes both a little bit more stressful. lol
alex,
love to catch lunch with you again sometime!
the challenge of being “home” while at home is definitely tough. trying to work this out with the help fo my wife!
I can’t come up with a reason to say I miss the corporate world, Sorry!! I very much need community but can find this without giving up my flexibility to live in Big, Inc.
chris,
love it. seriously.
Well guys, I am still making that transition from Corporate America to being at home and working. At this point the transition is not as fast as I would like but GOD is guiding my steps. I have the numbers down on what production I need in order to leave Corporate America for good. So once I hit those numbers or come as close to them as possible. I will be able to walk away. It will happen. So John, I know with a family it was tough for you to take the leap. But if you never do.. Most won’t!
lincoln,
i’m so encouraged to hear about your steps forward. it can take some time but don’t feel pressured… no one’s forcing you out…!
stay above board and know that the timing is somewhat out of your hands!
I miss the structure of the corporate environment. The most difficult task working from home for me has been creating a structure for me to work in.
Part of the joy of working-for-yourself is leaving this structure, but not having someone telling me what’s most important to work on has drained on me a bit. Sometimes I have to guess and find out later that what I was doing didn’t work out. When I worked for a business those things weren’t a big deal, now that I work for myself they suddenly become days or even weeks of wasted time.
Even so, I’m happy to be “free” of the corporate structure. I like seeing what I’m working on grow. It’s stressful at times but a lot more fun than having a standard 9-to-5 job.
i like some things about the structure, more specifically some of the expectations that help ease decision-making.
The thing I would miss most would be the time I spend with the children that are in my story time classes. Also I would miss the different people coming in getting books and video, dvd.
Also I need structure so working outside the home is better.
Bonnie
bonnie,
good points. structure is very important!
After leaving the corporate world, I lost my competitive edge fast. It’s taken me years to regain that and to learn to compete against myself. It’s hard to do at first, but once you get the hang of it, there’s no turning back to the cube.
chris,
that’s a good point. competition for me is very important!
Still in the corporate world, but I love it. The culture of our environment has lots of freedom, so no micro-managing takes place. Expectations are defined and friendly competition keeps us firing on all cylinders. I don’t think I would want to leap out. Enjoy the community and accountability of it all.
Good thoughts John.
justin,
you must be in a great environment! how big is the org?
Love that Dilbert cartoon!
dilbert explains life for me.
I’m making that jump now! Tomorrow will be the first day of my last week. Then it’s self employment from there. Excited, nervous and thrilled to see what happens.
WAH? are you ready…..!?
i’d love to hear more!
Totally ready! I’ve been planning it out. The cash cushion is in the bank, the work is very steady and income is coming from several different sources. I’ll mainly be working for a marketing company with lots of freelance work and a good bit of music work in there as well.
I’m excited and my wife is excited. I just have to push through this last week at my job. I can see the light at the end of the tunnel.
awesome! congrats man! that’s huge!