29 Reasons Why Being A Part Time Entreprenuer Sucks

by The Happy Rock on July 10, 2009


I know this may not be the inspirational pie in the sky post you want to hear, but it is reality.  If you are already a part time entrepreneur, solo entrepreneur, or blogger you can probably empathize with this list.  Better yet it might help you gain some insight into your own circumstances.

For those that are considering embarking on such a journey, this is fair warning.  This article isn’t an attempt to discourage you at all, but rather an attempt to prepare you for what lies ahead.   It may discourage you, and if it does then you probably aren’t ready yet.

Anyone attempting to augment their income through their own creative effort WILL have to deal with these issues.   This article isn’t an attempt to solve these problems, as I can’t claim success…yet, but I can claim to be actively attacking each one of these obstacles to success.   This article is an attempt to take ownership of the baggage that I have been carrying since I started.  If I am not honest with myself, I am only setting myself up for failure.

The inspiration for this list comes from my 6+ years of seeking extra income through a variety of avenues: online poker, stocks, blogging, web development, and running a service website.  I have also connected with others marching on their own journeys.  All of these are common roadblocks that will be faced by all types of entrepreneurs.

29 Roadblocks To Solo Entrepreneur Success

  1. Too much to do. The todo list is relentless and one person can only accomplish so much.  There will always be more you can do.
  2. Not enough time. This isn’t just because your todo list is 100’s of items long, but because you have the rest of your life to live.  A spouse, children, friends, career, shopping…that list goes on for miles too.  The couple of hours you have each night and on the weekends won’t feel like enough time to get the critical stuff done let alone the stuff you want to do.
  3. Learning. It takes a huge investment for on person to learn the vast range of skills necessary to succeed.  At least this list is finite though, although still humongous. Become a better writer, learn web development, practice networking, implement  marketing and advertising, craft your search engine optimization, research, accounting, customer service, and more.
  4. Sacrifice. You can’t do it all.  Areas of your life will suffer and gather cobwebs.  If it is important to you, other things must take a backseat.
  5. Discipline. Using time wisely. Getting to bed on time.  Being able to push through the dips and dead periods.  Discipline is required on almost all fronts.  You most likely don’t have enough yet.
  6. The world changes. Just as you begin to get a foothold, things will change.  Recession comes, technology changes the way people relate to your product, Google changes it search rankings, and competitors get better.  The world is in a constant state of change, so you have to be ready to ride the wave.
  7. Lack of feedback and accountability. Most people start their journeys alone.  Guess what, that means there is no one to provide helpful input or even constructive criticism on a regular basis.
  8. Competitors. There are plenty of other people and businesses trying to do the same thing you are.  While they have to face the same demons in this list too, there are also changing, adapting, and trying to be better then you.
  9. It’s consuming. At some point you will probably get so consumed with your side project that you won’t be able to stop thinking about it. You will be scheming at your ‘real’ job, as you go to bed, and while you are playing with your children.  It WILL take over your life.
  10. Criticism. Most people won’t get what your are doing.  When people don’t understand or don’t agree they try to convince you to stop. People don’t like new things and most are more willing to lend you a dose of discouragement rather than a helping hand.  Ironically, they think they are being helpful.
  11. So much you don’t know. This is related to learning, but uniquely describes the confusion and paralyzing effect that not knowing the right path can have on your side hustle.  There is no yellow brick road to follow.
  12. Too many options. Being in complete control affords you the power go in any and every direction with every choice.  While this is quite freeing it often makes things much more difficult.  Choosing between the best of two options is much easier than coming up with 20 great options and then having to pick the ‘right’ one.
  13. Luck. There is an element of luck that you really can’t control no matter how hard you try.  You can put yourself into the best position to get lucky more often than others, but you can’t fully control anything.  The person whose blog isn’t as good as yours may have randomly attracted the eye of a a major news outlet and get tons of traffic.  Stuff like that will happen.
  14. Watching other’s success. Seeing others succeed can be quite encouraging, inspirational, and educational, but other times it will frustrate you to tears.  It can leave you lamenting and disillusioned.
  15. No help. When you want go on vacation you can’t without major planning.  No breaks, you do everything.
  16. Slow going. For most of us success isn’t achieved over night, but you are so eager for it to happen.  You want it to happen so fast that you even take shortcuts just to get some positive results. Even then you won’t be able to see the benefit of most of your actions take until much later in the future.  No one will read your blog for months, but if you don’t suffer through those times you can’t get to the good stuff. The disparity between what you want to happen and what actually happens is torturous.
  17. Fear of failure. Trying to avoid failure is a recipe for failure.   You end up not providing enough value, because you are so focused on not losing rather than focusing on making your self irreplacable. The even more ironic part is that you will most likely fail. It is better to accept and embrace that fact now.
  18. Fear of success. It may sound a bit strange, but you may not be willing to do what others are doing to do to succeed.  The margnitude and force of this list will grow as your own success grows and you don’t look forward to that.   Maybe you are afriad to get too big or too well known. People might really notice and search information that you don’t want to come out.  Maybe just maybe you think becoming big will destroy your love for what you do.  You see examples of successful people who still aren’t happy and are in fact more miserable then when they started.
  19. Yourself. The same personality flaws that existed before you started will become even more visible.   Your procrastination will most likely get worse with more things to do.  Your shyness will hold your business back.   Without intentionally attacking your foibles, they will erode you chances at success.
  20. There is only one you. It is pretty darn hard to teach someone else to be you.  You think you know everything about how stuff works and how things should be, but that just makes it hard to give up control and get help.
  21. You can’t be perfect, although you want too.  You don’t have the time, knowledge, or money to make things exactly how you want them.  It just is, accept it. You have to be able to cope with making things that best you can in a short amount of time.
  22. You aren’t passionate about what you do. This is a quick recipe for failure.  If you don’t love what you do, you won’t be able to battle through the tough times.  Even if you do love what every it is you are trying to do, it will still be tough.  Your passion will be infectouous, so don’t leave home without it.
  23. Distracted by money. At some point you will start to lose authenticity and do things just because you can make money.  This isn’t something that is sustainable and often severely damages you long term goals.  Sometimes it turns a fun hobby that made some money into something that forces you to spend extra hours working each week.
  24. Sleep. You have a love/hate relationship with it.  You need it, but since you have so much to do you never get enough.  Without proper sleep your performance and mental capacities diminish and that slows you down, but you can’t get more sleep because there is too much to do.
  25. Imbalance. Your girlfriend complains that you don’t see enough of each other. The kids complain that you are on the computer all the time.  You can’t walk be the computer without checking something.  You can’t enjoy the weekend or vacation, because your todo list haunts you.  You eat out all the time because you don’t have time to cook.  You don’t exercise.  The sad part is that all of these types of concessions will effect your ability to sustain your output and desire  that is required for your long journey.
  26. The business is intrusive. This is different than consuming which describes the internal state of being uber-busyness.  Intrusive is more about the external demands on your life.  The email that has to be answered right now.  The website that goes down during dinner.  The important phone call while you are on a date.  The business wants to be first in your life, and it will scratch and claw to get there.
  27. Your other job. You will probably begin to despise it if you didn’t already.  It only interferes with your plans for world domination.  You will imagine all the wonderful things  you could do with all that extra time.   Or worse you will begin to use time at your career job to do side hustle stuff.  Amazingly it won’t be as hard to justify as you think.  At best this is a recipe for a horrible attitude at work and at worst would cause a job loss before you are ready.
  28. Burn out. It will come.  How can it not with such a list of daunting demons lurking at your side and only one person fighting the battle.
  29. It is hard. If anyone tells you differently, they were probably in the right place at the right time.  If you don’t think that it is hard after reading this list, than you better get started right away because you are destined for success.

{ 34 comments… read them below or add one }

John @ Curious Cat Investing Blog July 10, 2009 at 7:30 am

Great post. I think part time entrepreneurship is a great opportunity but it definitely has many challenges. My advice is to evaluate whether you can handle the above list and have the desire to succeed. If you are willing to work hard it can be a wonderful journey.


Neil July 10, 2009 at 8:06 am


The one about kids moaning that you are always on the competr really rings true for me. My 3-year-old will try her best to get between me and it risking injury either to herslef or the laptop in the process!


Kyle July 10, 2009 at 9:32 am

I totally agree with this list, I was just thinking the other day how much I just don’t have time for anymore that I used to do. I am going to have to do something to get back into running but my only option is to get up before my day job to do it, but if I do that I will be getting like 3 hours of sleep and… UGH!..


ChristianPF July 10, 2009 at 10:27 am

Wow, very detailed list – I can relate to most of them very well… You know, not to be “that guy”, but all these obstacles that need to be overcome are what makes it so rewarding when you reach your goal. Easy fought battles don’t mean much – it is the tough ones that you remember and take so much pride in winning…


ed July 10, 2009 at 10:54 am

Is fear of success simply “poor planning”?


Terri Zwierzynski July 10, 2009 at 1:06 pm

I’m curious, is your part-time status as an entrepreneur by choice? Or do you want to move to full-time, but don’t have enough income to make the leap? Are you making plans to go in that direction?

I’ve never been in this situation myself (my shift from employment to fulltime solo entrepreneurship was involuntary!) But it would seem that taking the plunge to go full-time helps you address these issues, mostly because you have more time (and flexibility). Of course they don’t go away; full-time entrepreneurs experience all of these too.


MoneyEnergy July 10, 2009 at 3:06 pm

I think it’s important to see this list – it also reminds me of graduate school, actually. The imbalance, not being able to do it all, the competition, the burn out. In fact, you could even *start out* passionate about your area/business and the demands can still burn you out. I don’t have easy solutions to any of it, I’m still in the middle of it. At least you are being honest with the situation which will better enable you to deal with it. And yeah, the role of “luck” is really annoying too (unless it’s happening to you, then it feels deserved:))


Chris Roland July 10, 2009 at 3:41 pm

This is an awesome list. I didn’t realize how much of my life was being consumed by what I am doing. It doesn’t seem like that much because I’m passionate about what I’m doing, but after going through this list, it makes me think.

I would love to see a follow up post on how to address some of the things in the list.


Monica Dennis July 10, 2009 at 3:51 pm

Trust me, even with a business partner like I have, this all still holds true. It’s having a full-time job that makes it all so hard but it’s worth it and we love what we do. Oh, and we’re single parent/married parent with rent/a mortgage so leaping from full-time job to full-time entrepreneur just isn’t prudent in our books.


The Happy Rock July 10, 2009 at 11:20 pm

@John – It is a wonderful journey because of this list in part.

@Neil – My little guy stands at my chair and says ‘Up’, ‘Up’, ‘Up’. That is when I know I am on the computer when I don’t need to be. I find its better to try and be in the moment rather than dividing my attention.

@Kyle – 3-5 hours of sleep is borderline destructive. Sounds like you might need to cut out some things to make everything better.

@ChristianPF – Great comment. Seconded.

@ed – I think fear of failure can be for a wide variety of reasons. Lack of confidence in your planning could be one of them.

@Terri – I would love to move full time, but for many of the reasons listed above, progress was slow the last year.

@MoneyEnergy – I love your luck quote. My MBA experience was easier than enterpenuership, because the goals are clearly defined and the path is straightforward and finite. I started heavily seeking many of my entrepreneurship goals during my MBA and that seemed easier than now. I know I didn’t have much time so my expectations were a lot lower.

@Chris A follow up post(s) is a great idea. Some experiments on how to handle some of these things would be quite interesting.

@Monica – I believe it doesn’t get any easier as things grow. Having partners probably blessing and a curse.


Finn July 11, 2009 at 10:38 am

You nailed it! all of these are realities of being an entrepreneur; so when my friends are asking my opinion about being a freelancer, I don’t hesitate in saying that entrepreneurship is harder than what it seems.


RB30RB40 July 12, 2009 at 8:49 pm

Oh wow, you hit the nail on the head with this one! “It’s consuming. At some point you will probably get so consumed with your side project that you won’t be able to stop thinking about it. You will be scheming at your ‘real’ job, as you go to bed, and while you are playing with your children. It WILL take over your life.”

I am so addicted and consumed by my new blog, I can’t even sleep! I went out til 3am Sun morning, woke up to play 2 hours of tennis from 8:30am-10:45am, had lunch, am exhausted, but can’t sleep b/c all i want to do is blog!!

Great post. I will follow.


Hiro July 12, 2009 at 10:03 pm

This is an awesome article..I couldn’t agree more with most of the lists you have there. I’m a part-timer myself and MAN does it take a lot of time and dedication…

Good luck to the rest of the part-timers


Bible Money Matters July 13, 2009 at 9:45 am

I can completely relate to a lot of these points – being an entrepreneur can really suck the life out of you from time to time. It’s a lot of hard work, and can be draining. I know that a lot of side hobbies that I had before starting my own blog have started to fall by the wayside, and a lot of my free time is tied up in blogging, my side design business, etc. I’m finding that I have to force myself to take time off and to spend time with others – or risk burning myself out. Toeing the line..

I look forward to the next post – 29 reasons why it rocks!


Journey July 13, 2009 at 1:42 pm

I am having this problem right now. I am freelance writing to earn extra money and it is hard. Some weeks I will make great money and have great assignments. Other weeks I have to pull teeth to get anything done because it is so boring. Right now, I am having a hard time finding new clients. I found a ton in June but it is getting slow now. I need to find more clients.


Alex Fayle | Someday Syndrome July 14, 2009 at 3:49 pm

These challenges don’t just bother part-time entrepreneurs. I work for myself full-time and I see myself in every single line.


car insurance phi July 15, 2009 at 8:55 pm

Wow, really comprehensive list. I’m one of those people who are about to embark on the same path and this post really sobers you up fast. Kind of funny, b/c it was a slap in the face but also motivates me more.


Liz @ ExtremeTelecommute July 16, 2009 at 4:50 pm

Great post! I’m working full time (and traveling almost full time) AND trying to build up a freelance business in my “spare” time. It’s killer. #27 is absolutely true–I’m find myself being oddly angry when I have to do agency work instead of build traffic. :)


Mrs. Micah July 17, 2009 at 9:56 am

Great post. After blogging for 2 years and consulting for over one I can say that every one of those 29 reasons is true over and over again.

That’s why I’m taking a July break from the blog work–I want to breathe, to catch up on the rest of my life, and at the end of the month I want to evaluate where I see this going. I’m not building it up to be a replacement for my full-time job, so it doesn’t have to be all-consuming and generate replacement income.


Andy July 17, 2009 at 3:02 pm

Great post and I could relate to almost evey item! Thanks for such honesty and saying what other’s wouldn’t.


Mouli Cohen July 18, 2009 at 6:04 pm

Don’t be discouraged, the rewards of entrepreneurship greatly outweigh any of the points you have on your list!


balor123 July 20, 2009 at 3:49 pm

Wow. Very well done. I also see a lot of that. Sadly, like a half built bridge, a idea not fully realized is usually useless, which is why it is so hard to be a part time entrepreneur. I still try nonetheless but try not to stress about it. Set aside a fixed budget for these pursuits and don’t manage that money like you would other money in your head. Keep trying in case the world suddenly becomes full of free time. This can happen because of a lull in weddings to attend for example. Or, because you were unexpectedly laid off. In these cases, you become the opportunistic entrepreneur, which while doesn’t guarantee you a good shot at it, maximizes opportunities over your lifetime.


Theo November 2, 2009 at 11:32 pm

Wow! Let me say that backward…Wow. I thought we were all alone. Not. Your article is good and very common for all of us who are making our way on the net. Nice work. Keep at it, sucess is for those who perservere.


Frank November 10, 2009 at 2:39 pm

I finally sat down today and read this post. Let me just say that I am glad I did. It is difficult pursuing a business while keeping your day job and saying “present” for the family. It’s good to know that others with the same goals are facing the same difficulties day in and day out.


Clayton Shumway November 25, 2009 at 3:34 pm

Great post…entrepreneurship is definitely not the easy way to fortune, in fact it’s probably the hardest! I appreciated the down-to-earth approach to your article.


Ben - BankAim September 20, 2011 at 5:32 pm

Very true.. but it can be a rewarding journey. I think a huge problem for entrepreneurs could be the constant checking of ‘stats’ and money earned, rather than getting work done and keeping on top of their niche.

If done right. entrepreneurship could definitely lead to fortune and early retirement, more so than working some 40 hour/week job.


Jason November 26, 2009 at 10:12 pm

Lack of criticism can be a problem. Many times family and friends will not visit your site. In other cases, they visit your site and won’t tell you the truth. Usually, it’s because they don’t want to hurt your feelings. In other cases, their criticism isn’t valuable. For example, some people are impressed by any site. On the other hand, more educated people will demand a more sophisticated site.

Therefore, get criticism early from webmaster forums.


Eleazar | Entrepinoy Bank April 17, 2010 at 12:00 pm

I was hit by Too Much To Do and I have not yet solidified my plan as an internet entrepreneur. This post is an eye opener for me to redefined my purpose and just focus on the essential things that will bring me to my goals.


Jim October 14, 2010 at 4:53 am


That is a great list. When you start out on your journey you read all the hype and the stories of how working for yourself for 2 hours a week will make you a millionaire. The reality is far different.

I am an online entrepreneur and I am currently putting in about 60 hours a week and have only just replaced my previous income as a sales manager. Entrepreneurship is TOUGH but ultimately well worth it, my advice would always be to go into it with your eyes wide open.


Natan January 20, 2011 at 4:29 pm

Good article. Before setting out, it’s really important to get into the right head space. A lot of first-timers don’t really view their business as an actual business. It’ll always be about the reader and the hardest thing for a marketer to accomplish is learning how to leverage themselves to benefit and serve others, not the other way around.


Paula @ AffordAnything.org August 4, 2011 at 5:58 pm

What a great list! There are a huge number of drawbacks to part-time entrepreneurship. I sometimes wonder how anyone with a full-time job manages to grow their blog to a solid base … blogging is SO time-consuming, I can’t imagine having to “go to work” (especially a demanding job) in addition to doing it! I have the benefit of being a full-time freelancer, so although my time gets split between blogging and other (paying) assignments, I still at least can set my schedule / say yes or no to clients.


Mike August 30, 2011 at 10:17 pm

This is the second article of yours I’ve read. You write very well.

Quite extensive on the cons but there are a lot more positive aspects. I imagine you experience those too or you wouldn’t be writing this blog which is definitely a part time business.


Dan - BankVibe September 15, 2011 at 6:44 am

You also have to be pretty versatile. You can’t, or dont have time to, specialize in one specific area which traditional employees have the luxury of doing. You have to be a sort of utility player in a way. With a web business, Im sure you’ve had to dabble in not only writing, but coding, web design and even sales.


Brian Johnson October 23, 2011 at 5:08 pm

I am starting to find that the time issue is a big one when starting a new blog. I won’t sacrifice my family time to grow the blog so that has been a struggle to juggle. Getting up early during the week and working on the blog before my day job has been helpful.

– Brian


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