How and where to start your own business or being your own boss?

Over the years, I have been working in different industries, but always within the IT department in different roles or capacity: Network Admin, Web Development, DBA … you name. I have about 12 years of experience in the field. On my spare time, I do lots of reading/research on SEO, web development, website flipping, selling/buying leads, Facebook pva and all of the alike. Yet, with all the knowledge and experience that I have, how come I don’t freelance? The answer is quite simple: I don’t really know how or where to start.

At the moment, I have a very stable and tolerable job! However, I am getting a bit tired of the office politics and dramas! I sometimes spend half to one hour overhearing others around my cube complaining about the house party that they didn’t get invited to, “I thought we were closed? How come I didn’t get invited to her/his house get-together?” Like it or not, such behaviors do spread and impact others’ workflow, unfortunately; well, that’s beside the point.

In addition, while I am qualified to do the job, do I actually enjoy it or being passionate about it? On a scale of 1 to 10—10 being the most passionate about—I would say that I am about a 6.5. Not too bad, yet not the most ideal either. The daily routine that sucks the life force out of most people for something that they neither care for nor enjoy; or, the motions and pretense that almost everyone felt victim to and a myriad of other reasons are all things that have started to make me think and see things differently.

To be blunt, I am well aware of the fact that freelancing or being your own boss is not really for the faint of heart. As the saying goes, “heavier is the head that wears the crown.” I know you can spend hours or even days working hard to achieve what you truly believe in, but at first the hard work might not yield much satisfying results. Losing money like crazy is a huge possibility; well, not “a possibility” it is rather part of the process, I dare say. The hours could virtually endless which could alienate most from certain aspects of everyday life, but I’ve made peace with that and willing to move forward anyway. If I like and love what I am doing, or more importantly believe in it, what’s working 48 hours straight to a guy like me?

Work setup: I already have a home office with pretty much almost every possible pieces of equipment that any normal office should have. There is no distraction at home. I even have my schedule on how to approach different things that are of interest to me, which is not really business related at the moment. In terms of disciplines and able to stay focus, that’s not a problem at all for me. I could write a guide on how to become a freelancer/your own boss; that’s how well I understand the subject and yet I am not doing it! Why? I don’t know where to start or how, I suppose.

What advice would you have for someone in my positions? Where would you suggest that I start? I have been on,, and similar websites. I am mostly monitoring, observing and drawing conclusions and what not. I guess, I need some pointers and guidance on where to start. Any help and tips is really appreciated. Thank you so much everyone!


Ok, ask yourself and answer this question:

What kind of products or services do I want to offer to the world?

You haven’t been able to start because you haven’t put yourself out there, you haven’t told anybody yet that you’re available for hire. But if you shouted “I’m available for hire, hire me!” from the top of the tallest mountain, some people who would hear you would ask you: ok, but what do you do?

Answer that first.

The answer to that question is a blend of:

  • what you are passionate about
  • what the market needs right now, or will need in the future (not what the market needed in the past!)
  • what you’re skilled at

For example, I can tell you that software companies and startups need server administrators on retainers to manage their servers 24/7. A great network admin who is also knowledgeable in web development is even more valuable.

That’s just one example of productized consulting you could offer. What excites you?


I can’t re-emphasize enough the points that @luckyisgood is making here.

Don’t try to do everything, either. You sound like you have a varied skill set. Find whatever really makes you passionate, and what will make you good money, and focus. Find jobs in that category.

Local work will almost always be more lucrative unless you live in a really bad area for it. Online work will almost always be easier - less in person meetings, less showing up at a client office “just because in person is better” etc - big time sinks. For online work, find a niche and don’t be afraid to stick to it. If your necessary income puts you in a bracket well above the fierce competition for the cheapest labor - don’t compete with them. Apply to high value or high paid hourly jobs and ignore the cheap bidding ones. There’s still plenty out there.

But first, as stated above - find out what you want to do - if that’s one of your major reasons for leaving full time work, ensure that the move is worth the risk! Do what you want to do. And find the drive to succeed. The hardest part will be starting out, and finding work when you have none.

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Great points, @jeffreylees. So, for now, we have these steps (I agree with them):

  1. Find out what you want to do,
  2. Focus (specialize / pick a niche)
  3. Set starting pricing plans (pricing determines who your clients and competitors are / aren’t)

The next move could be to:

  1. Create a basic online presence (website, email list, preferred social channels if any / applicable to Sam’s business)
  2. Go look for clients (when Sam finds them, he can show them his website)
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Howdy Y’All,

First and foremost, I want to thank all of you for your great advice and support. I was traveling for the holidays to see families before Santa comes into town, so I wasn’t available to reply sooner. In any case, both of you provided some valuable pointers and great insights. Awesome! Thank you!

I did try for almost a year to market myself and making myself available out there. I came across some projects on Freelancer where the demands and requirements were so high and the payout weren’t really much to consider. I said to myself, oh well, you have to start somewhere to make a name for yourself, thus begun my long dreadful journey bidding for projects that were somewhat unreasonable.

The biddings were in themselves a convoluted process, but it’s all in hope of making a name for yourself, right? I knew what I was getting myself into, so I didn’t mind but I never got a single client even though I was willing to lower my standards to the to the bottom of the ocean.

In terms of what I am passionate about, what the market needs right now and what I am skilled at is a bit tricky but should definitely be one of the places I start looking to reshape myself. Skills? Wow! I am usually the Swiss-Army-Knife guy or the Jack-of-all-Trade for my department. Flexible and knowledgeable about so many different things.

While that was always a good thing for me in terms of “a job” I came to the realization that it wasn’t a good practice for the long-run. I was NOT an expert in anything; I simply knew enough about everything to be dangerous. Now, I am putting an end to this practice. My only primary area of focus is SQL and Linux/UNIX Admin. For SQL, the ones that I going for certification at the moment is Microsoft SQL Server 2012 (made up of 3 exams), and then I will go for the Oracle DBA Certification. The other thing is go for the Red Hat Linux Administrator Certification as well, I already finish one of the course; I only have one more to go.

The certifications are not really mandatory, but I want to be as legit and official as Rockingham Castle. I want to be the guy who has the experience, the certification and the degree. Either that intimidates a client or it makes them feel in good hands assigning their projects to me.

As Luckyisgood said, I need to start making a name for myself, and one of my goals at the moment, while I am sharpening some of my skills is be more active here on SitePoint. I have to start somewhere, right? :wink: I don’t know how it’s gonna go, but certifications can never hurt lol. Two or three posts a week within the Database and Linux forums should be sufficient enough to keep a good presence within the community.

Jeffreyless, you are absolutely right: I have been trying to do everything myself. What a concept! Silly me, I tell ya. Finding work when starting out is never easy. As I mentioned above, I spent a whole year and never got a single contract. Hey, no biggie, it’s all part of the game.


Sounds like a good plan, @SamGrayson!

You could also define who your ideal customer is, so you can better focus your efforts in helping people online with your skills and knowledge. For example, if you define that your ideal customer are IT managers in small to medium companies, you could brainstorm all the ways how to reach them and make a name for yourself in a way that they notice.

Or, maybe you decide that you’d rather work with startups, or maybe experienced IT companies, who need an outside consultant. That’s a different customer category, and the approach is different, where you hang out to reach them will be different.

Knowing who your customer is, and where they hang out, and how they prefer to be reached, is something I’d definitely spend at least a day brainstorming. Now that you know what you want to do, it’s time to prioritize your time and how you spend it marketing yourself. You strike me as a person who’d do very well writing about what you do; content marketing is a long-term strategy but it pays well if you keep at it.

Good luck!


It’s ironic that you mentioned about writing. What do you mean by “writing about what you do”? Would you be willing to elaborate a little bit more on that? What is content marketing?

No problem @SamGrayson. “Writing about what you do” could mean maintaining a simple blog on your business domain. Content marketing = getting business leads by teaching the market first about the problems that you solve.

For example, not all of your customers are aware of i.e. security holes on their servers. By publishing interesting and educational content, you can establish yourself as an authority in your field. That’s a lot of work and definitely does not bring customers over night.

Examples of good content marketing: - a guy is publishing articles mainly via email, and also via his website. Imagine how much business this can generate (my guess is that his customers are developers who at some point say “screw it, this server administration is too tough for me right now and I don’t have time, I’m gonna contact that guy that’s been teaching me server administration in the past six months, to fix my server”.

Alternative to content marketing is having money for ads and sponsorships and whatnot. Content marketing: slow & steady. The best way to market your business is a mix of proven tactics, and producing content is almost always part of it now. Every business is a publishing company now.

I’d be happy to answer more of your questions. Content has helped me build my agency in the past and I’m using it right now for my new product business.

Thank you so much, Luckyisgood! I really appreciate the pointers and guidance.

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