The Problems with Entrepreneurship

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Photo courtesy fabiogiolito

So here we are, late at night working away. I’m a 30 year old entrepreneur/hacker/business man. I write code because it helps me to do business deals. We’ve rehashed this conversation over and over again.

“You just sit here and work,” she says.

“It’s what I do.” I tell her. “It’s like playing tennis or singing. This is what I enjoy doing.”

And again, we are both hurt by the other person. Not because we’re intentionally hurting each other, but because it’s hard when an extrovert web programmer gets together with an introvert normal person.

The problems with entrepreneurship - freedom

Most of the time, I love being an entrepreneur. Most of the time. Other times, I hate that I enjoy it so much. Entrepreneurs struggle with time management - our biggest enemy. We struggle with balance because most of us have 40-60 hour work weeks already. Many of us work for startups who need more time than a typical corporate job. But we can’t help it. We can’t work for larger businesses. They’re stifling, stuffy, restrictive. We need freedom.

So, we start our own things in basements, spare bedrooms, garages and kitchen tables. We carve out just a few more hours out of the week to work on something that could give us that freedom. We crave that freedom. We need the air to be our air, the land we walk on to be our land, and the time we live to be our time.

But by carving out just a few more hours a week we strain our relationships with those who aren’t involved in our adventures - our internal hopes and escapades. We lose touch sometimes. We forget often.

That freedom we’re driving forward for so badly, is it worth it? Sometimes, I think it’s not.

I once took a job at a larger organization with the intention of staying the course and simply doing my duty - providing for my family, coming home at 5:00, not having those side projects take up my time.

It didn’t work. I felt like I was a rat in a cage. I lasted 2 months.

The joys of entrepreneurship - the hope

So, here’s my question. Is it worth it?

When we finally get to the destination we’re hoping to make it to, is it worth the effort? I want your stories. I want to hear about your pain, and your joy. What is it that makes you tick? How do you handle the problems of entrepreneurship? And, in the end, is it worth it?

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22 Responses

  1. Carl's Gravatar

    Posted by Carl on Jan 28, 2007 at 11:37am

    I can sympathize with your comment about time. Most often people who are jazzed up about something just can work for hours. I find I can go several hours, skip lunch because of being wrapped up in some project or idea. Those that don’t share the same interest can’t always relate. I don’t think that is really bad, just different. Thanks.

  2. Brian Balfour's Gravatar

    Posted by Brian Balfour on Jan 28, 2007 at 12:09pm

    Nate,

    Great post…I couldn’t have said it better.

    I have had a lot of small successes with entrepreneurship. Every one just leaves me wanting more. It gets to the point where I ask, will it ever end? Will I ever be satisified? Is this good or bad?

    I don’t know. The only thing I do know is that the thought of working for a large corporation for a number of years bores me to tears.

  3. nate's Gravatar

    Posted by nate on Jan 28, 2007 at 04:35pm

    Carl and Brian,

    Absolutely! When I used to freelance as my singular source of income, I actually had to set timers to remind myself to eat or take a walk or something. But, I found that while I was freelancing, I actually spent more time with my wife and friends because I was spending those 40+ hours a week doing _exactly_ what I wanted to do.

    Now, with a full time job — even one I enjoy — it’s not _exactly_ what I want to do, but it’s close. So, I spend so much time attempting to my thing that it sometimes gets in the way of other priorities, but I do it just to feel “normal”. Many people don’t understand that.

    Have you guys found yourselves spending more or less time with other people when you are an employee for someone else? Or vice versa for when you’re the boss of your own thing?

  4. drawkbox's Gravatar

    Posted by drawkbox on Jan 28, 2007 at 08:20pm

    When you are in the zone, you are in the zone. Programming or design takes a dedicated period of time before all the project tentacles are organized into your mind memory space. Those times are needed and yes sometimes they can run well thorugh the night, 10+ hours etc. Its very important to succeed or work heavily to make it there. The worst is to not fulfill your dreams for other people, you will end up despising them. Better case is bring them into your world. Creativity is pretty addicting to anyone.

  5. nate's Gravatar

    Posted by nate on Jan 28, 2007 at 09:42pm

    outstanding point drawkbox.

  6. Helen Baxter's Gravatar

    Posted by Helen Baxter on Jan 29, 2007 at 02:24am

    It is always worth it. The ultimate freedom is to spend your life doing what you love with people you like.

  7. Jed's Gravatar

    Posted by Jed on Jan 29, 2007 at 09:40am

    I agree with Helen—key word being “always.” Yes, it’s always worth it.

    I often think in terms of destinations, but I try not to. I think the best barometer I can use to determine if it’s worth it, is how I feel right now.

    Why do I believe that? Because it’s always right now.

    For me, nothing’s worth feeling hopeless, or imprisoned, or like I have no say in my work—I become miserable and bored and boring. My loved ones wouldn’t have me that way.

    Still, yeah, it’s hard. But hard’s not always bad.

  8. Brian Balfour's Gravatar

    Posted by Brian Balfour on Jan 29, 2007 at 02:17pm

    “Have you guys found yourselves spending more or less time with other people when you are an employee for someone else? Or vice versa for when you’re the boss of your own thing?”

    Definitely spent more time with others when I worked for myself.

  9. Flee The Cube's Gravatar

    Posted by Flee The Cube on Jan 29, 2007 at 10:28pm

    My relationships were better when I was working for someone else because I was working exactly 40 hours a week at a low stress job. But I felt like I was going nowhere, and despite the laid back atmosphere, the job felt stifling. At least now I don’t feel stifled, but the stress and uncertainty definitely put a palpable strain on my relationships.

  10. nate's Gravatar

    Posted by nate on Jan 29, 2007 at 11:15pm

    Thanks guys! I think you’re all right on. I love that you’re all so honest about it all.

    Helen - “The ultimate freedom is to spend your life doing what you love with people you like.” 100% right on! I’m fully with that idea!

    Brian - I also find that I spent more time with others when I worked for myself.

    Flee the cube - What was it about working for yourself that made you stressed out? I’m curious because it seems that I’m exactly the opposite. Working for others seems to stress me out more than working for myself (except for the random paycheck thing. If it were more consistent, it would be cake for me).

  11. Berry's Gravatar

    Posted by Berry on Jan 30, 2007 at 12:25am

    I have nightmares about having a job. I sold my office supply business last March because just making good money was not enough for me… I wanted to make good money doing something fresh, cool, and helpful.

    Nate, if you need someone to do small coding projects for a small amount of money get in touch with me. I have a guy I work with that is great.

  12. Erin's Gravatar

    Posted by Erin on Jan 31, 2007 at 11:53am

    If I ever have a good enough idea, I might understand what you are on about. I do not begrudge any entrepreneur his time spent on good projects, provided there is some evidence the projects are, in fact, good.

    I don’t understand why anyone’s identity has to be so tied up with their job, which is what you communicate with that “rat in a cage” sentiment. But that’s really a separate issue from what you’re trying to talk about here.

    To me, work is work, and life is everything else. I like to spend my whoa-did-I-really-just-spend-that-many-hours-on-that project hours on art and craftwork.

  13. nate's Gravatar

    Posted by nate on Jan 31, 2007 at 12:14pm

    Berry - thanks for the offer, and I may, in fact, contact you as I do need someone to finish up a small project for me.

    Erin - I didn’t mean to communicate that my identity is tied up in my job with the “rat in a cage” comment. However, I can see how that came across now. Instead, I was hoping to convey that I felt like I was restricted in what my job duties entailed. I like the freedom to do cool things when I feel like it, and to do mundane things that need getting done when I feel like it. I don’t particularly like people giving me tasks to do that I don’t want to do. Something about it feels wrong to me, and I feel trapped under the “employer’s” finger rather than having some sort of autonomy, responsibility, and authority all at roughly the same levels, and reasonably high levels (since I feel reasonably confident in my abilities).

  14. Zach Braiker's Gravatar

    Posted by Zach Braiker on Feb 01, 2007 at 09:52pm

    An entrepreneur is an artist. An entrepreneur must create. It has nothing to do with wealth. It has nothing to do with success. It is a compulsion to create, and if you can stop, then stop. But if you can’t stop, if you are driven to read one more article at 5 am, question how everything works even though you wish you could let your mind rest, and develop an idea because it must grow, then you are an entrepreneur.

    It’s hard for people who don’t experience what we experience to get it. 15-hour days aren’t 15-hour days. They are thrilling, alive and exciting. Because we are growing something that is ours, turning a thought into a reality.

  15. nate's Gravatar

    Posted by nate on Feb 02, 2007 at 07:56am

    Aw, you guys make me want to weep. It’s a great thing to be surrounded by people who “get it.”

    I fully am with you Zach.

  16. Brad Fults's Gravatar

    Posted by Brad Fults on Feb 02, 2007 at 08:56am

    I thoroughly enjoyed the thoughts sparked by this post.

    It is, of course, more awesome to do exactly what you want to do for the “work” hours in a week. Whether it’s freelance work or taking a chance with your own startup, people like us can’t be pacified into mundanity for mere practical concerns.

    Not to sound too corny, but I think it’s the same motivating factor behind the Founding Fathers and the American Revolution — freedom is the ultimate goal, not comfortable living. Comfortable living would be nice to have, but without freedom it’s only a jail cell with padded walls.

    That emotional and creative freedom is of paramount importance not only to any single person’s life as a means to happiness, but also to humanity as a whole because true genius and historic accomplishments stem from a person’s raw creative power applied in new and eccentric ways.

  17. misha's Gravatar

    Posted by misha on Feb 02, 2007 at 11:15am

    Interesting post, friend.

    I think ultimately you have to decide your values first and then choose your work. If they gel - you are one of the few and the lucky. But work and values and what we love to do won’t and can’t always match. Because we are here not just for ourselves.

    There will be years where they do - I had some and they were wonderful.
    But whether it’s by having children, sickness and coming to terms with our limitations, marriage, getting laid off…something, someday is going to teach us that life is not about doing what we are or having to do what we love. Life is about serving. Giving. Enjoying. Loving. Living. And doing all of that with healthy boundaries and honest feedback that we listen to and ask for.

    That’s maturity.

    And I’m not saying you aren’t (heck, we own stock in your fan club) - but I am saying that it’s probably asking the wrong question.

    Of course people will relate to this. I am an entrepeneur of a different ilk now. A mama who created a company of four. Do I love what I do? On the good days. Do I love to create, dream…I write code on hearts! In developing brains… But fredom is illusive. And costly. And sometimes we have to choose between that and deeper relationships. To have a deeper life.

    So entrepeneurship for the sake of freedom - is it worth it? Of course not. Not if you are sacrificing something or someone. Is it possible to have both? Of course. But not both, all the time.

    I still believe in loosing our lives we find them. So unpopular, but I think we do find them eventually. But we have to know when to choose to loose them, too.

    But then that is because relationship is more important to me than freedom. It wasn’t always, though.

  18. Helen Baxter's Gravatar

    Posted by Helen Baxter on Feb 02, 2007 at 03:24pm

    It’s not about the amount of hours you put in. It’s about enjoying the processing and getting results. Like Zach says: “An entrepreneur is an artist. An entrepreneur must create. “

  19. Carl's Gravatar

    Posted by Carl on Feb 04, 2007 at 06:55pm

    I find that my work time is so flexible I can usually fit “something” or “somebody” in. Often I work my schedule around family things or some need I have. I have wierd work situation where I do work for “the man” but I have a high degree of flexibility in that job ( I’m remote) and I work on a small startup team within the larger firm ( a big mega-jumbo multinational ).

    I find that I spend time in waves - working longer and traveling more in the fall - winter and early spring so I can have more time off in the summer.

    I have one hard and fast rule- I quit at 3PM on Fridays.

    Nice thread of discussion here. Thanks!

  20. Helen Baxter's Gravatar

    Posted by Helen Baxter on Feb 05, 2007 at 03:52pm

    Even at start up when you put in all the hours you can, it’s important to take time out for fun & friends.

    I definitely works in chunks that fit round the seasons. I never mind working long hours in the winter, but in the summer I make sure I kick right back.

  21. ejoe's Gravatar

    Posted by ejoe on Aug 19, 2007 at 01:45am

    I think the point isn’t to view it as an “end” but a journey where you enjoy the process.

    The time and workaholic tendencies of an entrepreneurship can be tough, but that is where yo have to leverage those entrepreneurship skills and find more efficient ways to automate things and offload work until you do feel like you have a good balance in life and work.

    the 4 hour work week is a good book that describes a lot of those techniques and is quite an inspirational book as well.

  22. nate's Gravatar

    Posted by nate on Aug 21, 2007 at 11:46am

    Comfortable living would be nice to have, but without freedom it’s only a jail cell with padded walls.

    That quote is the truth! Well put, Brad.

    yo[u] have to leverage those entrepreneurship skills and find more efficient ways to automate things and offload work until you do feel like you have a good balance in life and work.

    And that is exactly where I start to find the balance again. Offloading work to others, or just simply doing triage on my projects is the beginning of sanity when I get overworked. And yes, if any of you haven’t read the 4-Hour Workweek, you should. That book is the culmination of 15 years of my thoughts. We’ll be using that book as a reference for years to come.

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