Dear SQL DBA: I Want to Work for Myself (video with captions and transcript)

Our question this week comes from an IT pro who would like to be self-employed. In this episode, I talk about three big things you need to think about to start working for yourself, and two possible paths to get there.


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Welcome to the Dear SQL DBA podcast and YouTube show. I’m Kendra Little. On today’s podcast, our topic is Dear SQL DBA: I Want To Work For Myself.

For the Dear SQL DBA podcast, I take questions from folks, database administrators and developers usually, and they give me all sorts of questions.

This one is someone who said,

I currently work for a larger corporation as a consultant. There are lots and lots of processes, and all of the tickets I work on are emergencies and I’m getting really burnt out. “I have an IT focus. Is it possible to get a job like a freelance developer but with an IT focus?

This is a question that, it’s a great question, and more and more freelancers find different ways to do their jobs but freelancing isn’t easy. I will mostly be focusing on working for yourself in The United States today. There’s different people who do this around the world and with different healthcare systems and different tax laws, it does vary.

My experience with this is all in The United States, and in The United States, freelancing isn’t easy. I don’t get the impression that it’s super easy anywhere but we do have some of our specific challenges.

Three big questions

One of the big things to look at first when you’re thinking about starting to work for yourself is three big questions.

What are the products or services I’m going to sell? When I say products here, I really mean what am I selling? They may be all service based. There may be some product I actually deliver something, but what am I going to sell? Who am I going to sell it to and then how will I go about running the business? So, we’re going to dig into each of these three things because before you get started, you need to know what you want to do with all of these.

What do I want to sell?

Will I build some tools that I will need to do my services or am I going to sell these tools to people? What types of processes do I need to build my services? Even for an initial consulting job, what kinds of scripts do I want to use? I can’t just use anyone’s code from the internet. I need to look at their licensing.

What kind of tools do I want to use for the product that I’m offering, how long is it going to take me to set up that initial offering? What do these products cost?

And are there products I can sell that once I build them first, they will continue to make money for me without me actively being involved in them? This isn’t always the case but sometimes, there are products you can build where for an initial effort, those products can continue to generate money with relatively low maintenance or input on your part, where all of the work is done by a tool you built, perhaps. It could be a variety of things but you’re not going to have to be personally delivering the product. Sometimes that’ll be a yes, sometimes that’ll be a no, but you really just want to know the answers for these.

Who are my customers?

And then in terms of who you’re going to sell them to, there’s different ways to find your customers.

Some businesses run on customers that find them and come to them and maybe this works based on a blog, or maybe there are free tools that are given out. For instance, these days I write a free quiz every week. I have quizzes on my website, I also blog on my business website, I give away some courses for free.

Doing these things so that when people are having a problem and they search in a search engine on the internet, you want to have them finding blog posts by you, or finding tools that you have if you want to have this type of relationship where the customer starts using your tools and then there’s perhaps something else that they can upgrade to that costs money with you. It takes a while to build up a following so that enough people are finding you, right? We have to start and we have to build this up.

There are businesses, however, where it’s marketing is done by, okay, we’re going to identify the customers, we’re going to purchase a mailing list from someone or we’re going to purchase a list of potential customers from someone and then we are going to reach out to these people. Course, we have to figure out how are we going to identify with them, who is going to be going out and engaging with them, how much time is that going to take?

And then we design, after we figure out, okay, who are our customers and how are we going to connect with them, we have to design a sales pipeline. Because we want to qualify our sales prospects. Depending on what you’re selling them, and in fact, I would say in general, there’s very few businesses where you want to sell your product to just anyone.

You want to sell your product to people who are going to find it useful. Because you know, selling something to someone that’s totally useless for them is going to get you bad reviews and unhappy customers. So, you need to have a process for your customers that you’ve identified to help say, “Is this right for you?” And we’re going to bring you down through the pipeline.

You want to think about when you’re working for yourself– one of the inherent problems with working for yourself, especially if you’re doing something like consulting is are you trying to land really large projects, or are you trying to work on a lot of different projects? How many customers do you want to have? If you want to do the kind of business where you’re working really with one or two customers at a time, the problem with running a company like that is that you become really, really dependent upon those customers, and this isn’t just tiny companies.

I worked for a software company with 100 people at one point where most of our revenue came from one really large customer. And when that customer says jump, it’s really hard to say it’s not a good idea to jump right now, because if they leave, there goes a huge amount of your revenue stream. It can be done, it puts you into different situations in terms of your relationship with that customer. And these are all things that we’re talking about.

You can change these over the life of your business. What we’re talking about here is saying for the initial offering that I want to set up, what do I want to do?

How do I run the business?

There’s also a lot to think about just as to what business do I want to form? Am I going to have partners? How am I going to incorporate this legally? In The United States, you can do this as an LLC, you can do this as an S corp, there’s a lot of different ways. Put some time into researching what these different things mean, and figuring out what you want to do.

You also have to decide how much money you want to invest to get started. Because especially if this is something you’re going to jump into full-time without a customer pipeline, you’re going to burn through money.

You’re not going to have a lot of income coming in unless you get really, really lucky. So, you have to figure out how much am I going to invest and how much risk will I tolerate? Even in small business where things are going well, and you do have good income for a while, there can be these dry spells. It may be based on time of year, depending on the industry you’re using, it may just be a coincidence. I’ve actually seen in the consulting business that there are seasonal dips in consulting where people are like, “Oh, well, it’s summer vacation, “and everybody’s going out with their kids, “we don’t want to do a lot of research into changing things. “we’re just keeping the staff around “just to keep things steady.” If you’re providing more sustaining, regular services for people, that might actually be your higher period if people are out of the office and they want you there to help sustain things.

So, depending on what your industry is, there are going to be periods where things wax and wane and you do need to work that into your risk calculation. When you’re working for yourself, you can’t count on always getting the same paycheck for the right amount coming in. Do you want to have people who contract as your employees? Do you want to have employees? Especially in the initial years of your business, it’s a big decision, and then just, how am I going to run things?

How will I keep track of who my customers are, their contact details, how I have engaged with them, how likely I think they are to buy a service? There’s tools you can use for this, you may want to start using something simple, and then grow, depending on what kind of potential customers you’re starting with, you may need a more complex tool if you actually already have a good base of prospects that maybe you’ve purchased from someone or have some way to access. Need to find ways to invoice people and to track our expenses, very important. We need to do bookkeeping and accounting, and there’s just a lot of mundane little things that come with doing your own thing. Like not only invoicing people, but following up and saying, “Hey, I need to get paid.”

So, there’s lots and lots of different things to start with just on running the business side. How do I get to this path though, right? I need to think about my products, I need to think about my customers, I need to think about how to run the business.

Path #1: The Expert

But okay, how do I even get the ability to attract the customers? There’s a couple different paths that I’ve seen folks take to this and I’m going to outline two of them.

We have a question that fits right in with the first path. The question is, “How do you stand out from the other more experienced consulting folks?”

So, let’s talk about this in the path to the expert. One way to become a successful freelancer is to figure out: these are the problems I want to solve, these are the products I want to sell, and my customers will want to buy them because they want to do something faster, or there’s something they can’t do that I will enable them to do. Or they won’t have to have as, they’ll be able to save costs in some way. Once you identify what this really is, you can work towards becoming an expert and really focus on, especially these things that you want to offer.

Now, you’re not going to dive in with this path. Folks following this path tend to say, okay, I want to work for myself.

One of the first steps to doing that is I need to learn how you’re going to run this business. I need to learn how to attract these customers so I’m going to find a small to medium sized business doing something similar to what I want to do, at least in that industry, and I want to work there for a while. I want to learn from them, how they are running and growing that business, and what works and what doesn’t, and while I work there, I am going to build up a personal blog and a lot of my own intellectual property, and when I’m doing this on my own time, this is not part of the company, this thing I’m doing on my own time, when I’m doing this, I’m really going to focus about building up information that is related to the services or products that I plan to offer.

That intellectual property that you’re building up, speaking at conferences, doing that blog, is what is going to set you out once you eventually strike, it’s going to set you apart rather, once you eventually strike out upon your own as an expert and it’s really that focus on exactly what you offer and your approach to it that is going to set you apart. So, you want to have some personality in there and you want, maybe this is going to give you a, depending on what you want to deliver to people, maybe this is going to give you a focus on, okay, I’ll include some short video clips so if I want to do consulting, so they get a sense of what it’s like to talk to me, for example.

Or, if you’re going to offer something more automated, maybe you want to start building small example services or building small examples of the types of things that you want to do.

There are things we have to really look out for in this path and you have to be careful though. When you’re working at a small to medium firm, I mean most of the times, there’s going to be an agreement that says, “Hey, if you leave us, you can’t take our customers with you.” I’m not going to get into arguing about legal enforceability. You really don’t want to be stealing customers anyway. I’m not saying to get a job at one of these small businesses so that when you go work on your own, you can take the clients, because usually, that is going to light a giant bridge on fire and cause a ton of problems.

I would be pretty open in the interview with a company like this saying, I would perhaps, because at this point, when you’re getting the job for the company, you don’t know. I mean, you may find that you really like working at this little company and you’re like, “I don’t need to go work for myself, this is actually so rewarding, I don’t want to deal with all that accounting and bookkeeping, this is better.”

But I would be open if you are thinking about maybe doing something yourself someday. I would be actually open about that and honest about that because in your relationship with that employer, you don’t want to have a big giant secret that you’re hiding, in my opinion.

Also, that opens up the door to have a conversation with them that says, “If I’m writing blog posts on my own time, who do those belong to?” You want it to be very clear if you’re on the side building up a presence for yourself, you want it to be very, very clear that you own that intellectual property.

Same thing with talks that you write for conferences. You want to know exactly which ones you own and exactly which ones your employer owns. Because if there’s a point where you do set out on your own and you start using these materials, you really don’t want to get hit with legal problems at that point when you’re just starting out your own company.

So, I would negotiate for is it okay for me to own this intellectual property that I write, who owns that?

I would raise the question, and make sure you clearly know the answer to, is it okay for me to moonlight on something? Can I take on clients on my own in hours outside of working hours that are totally separate, can I do work on my own and get paid for that? This includes even, like if you do say a pre-conference session at a conference, these are paid engagements, and so, knowing that even helps, yes, you’re taking on outside employment, is that something that they don’t allow? Because if so, you may not want to work for them if you really are setting the stage to go work on your own. So that’s Path A, or Path 1. I should stick with the numbering system.

Path #2: The Side Hustle

The second path is the side hustle because on Path 1 we were really, we’re doing some blogging on our spare time, but we weren’t really doing moonlighting in our spare time. And maybe it comes up when it comes to conference talk, but we really working a second job. The second path to this isn’t really becoming an expert. The second path for this is working a lot to make it happen, and by a lot, I do mean a lot, there are folks who do this.

Starting a second business in your spare time and scoping your products to fit it to make sure that okay, I am working multiple jobs. If my customer needs me and I’m working my main job, I need to have a way that that’s okay, where they don’t need an immediate response or maybe I have some job where I can stop working it for a while, most IT jobs aren’t like that, they’re full-time jobs, right? Usually, we commit to these certain hours but you need to find a way to make sure that for your side gig that okay, I’m only available during a certain time, or there’s a long enough response time, a long enough service level agreement for you to not be available right away, typically.

So, you start off doing something nights and weekends, you scope your products to fit with that, and you use that experience to refine your product and figure out what works really well, to build up testimonials from your customers, to get all your processes set, to get your accounting set, ‘cause you’re doing this in your spare time and as you’re scaling up your business, you’re saying, I’m going to get to certain point where I can leave that original gig and do this side gig full-time.

Again with this one, you really have to make sure that you’re not secretly doing that work ‘cause you’re employer is going to find out. The more successful your side gig gets, the emplo– But also, you need to be able to be open about this. You need to be able to have a with and say, hey, you know, this is what I do and this is how I do it well to be open with not only your existing customers but to have a way to communicate with potential customers.

The biggest problem with this is also that it’s really hard, it’s really time consuming because we’re dependent upon the revenue from our initial job. While we’re building up the new one, we are literally rebuilding our career as we are working it.

What about contracting?

I’ve had some folks ask me also what about contracting, can contracting be a stepping stone to make this process easier? I personally have been a contractor before. I was a contractor at Microsoft and these terms for folks outside The United States, these terms might work a little bit differently. In The United States, typically, a contractor works for an agency, the agency has a bunch of clients and they hire on contractors for short to medium term engagements, the contracting company takes a cut of your income and typically in The United States, you earn an hourly rate, you may or may not get any benefits for this, so you may still be buying your own health insurance separate from that.

The thing about my contracting gig is I actually, for me, it ended up in me getting a full-time job at Microsoft. At that time in my career, what I really wanted was a “real DBA job.” I wanted to be a full-time DBA working on production systems. I’d essentially been a junior DBA and only gotten to work in non-production systems up to that point. And I got this contract gig, and I also was like, I wasn’t sure what it would be like to work at Microsoft. I wasn’t sure if I’d like it, so it was kind of, you know, like a good short term opportunity to do that, and I could sustain risk at that point. Like if it didn’t work out, I could pick up another contract, I was okay with that, and my only dependent was a giant rabbit at that time. So, relatively low risk. It ended up getting a full-time job at Microsoft.

Looking back on it, it would not have been a good job in terms of going out to work on my own because I hadn’t negotiated a great rate. And a lot of that was I didn’t even know how to negotiate, and not knowing how to negotiate is a hindrance to when you’re working for yourself. I just wasn’t ready at that time. Also, I worked a lot of hours for that job and I needed to be available to work an on-call schedule that could be very erratic. And if I had tried to do that job and another job at the same time, I would have gotten burnt out. So, it just would not, that contracting job wouldn’t have worked for that.

If you can do contracting in a way where you can negotiate a really, a good rate, that allows you to, within a limited scoping hours of work, say okay, I’m earning enough here that I can do a side hustle, or I’m earning enough here that I have time to blog. I have time to build up my expertise, and this contracting job allows me to go on the expert path, you can do this.

But you really want to make sure that it is the type of job that isn’t going to burn you out. Then here’s the other thing, with contracting jobs, the contract can come to end at any time. The reason this is attractive to employers is you’re not a full-time employee. So, if they run out of budget, your gone. So, the biggest problem I think with contracting is you get the sort of uncertainty of what is my paycheck going to be next month? Without the benefits of working for yourself. You might be able to fit it in with this, but I don’t think it’s a magical way to speed up the process if that helps, it’s another job, but it’s a job with some uncertainty built into it. So, it can be a little tougher than having a more predictable full-time job if you’re trying to do the side hustle route.

I know this sounds hard and may sound a little bit discouraging. But it is hard. There’s a reason that not everyone is doing this.

There’s a reason that you see people strike out on their own and then take a job at a full-time company again. It doesn’t always work well, and you will, when running your own business, you will have to go through a process of saying, “Oh, this didn’t work out. I wasn’t charging enough money for this / I need to change my product or I need to raise my rates,” or, “I’ve lost clients and I need “to figure out a way to find new ones,” or, “I goofed up at this client. I need to see if I can save this relationship with my client and they may leave me.”

Goofing up may or may not be your fault. Goofing up can be a communication thing. It could have been a problem with a contract, it could have been in part someone else’s fault who works with the client, right? But things are going to happen and mistakes are going to be made, that’s just life.

So, you constantly have to be really persistent when working for yourself and say, “Okay, how can I make this better?” And “How can I get past this?” So, it’s hard, and there is a path from being really burnt out to being a consultant who works for themselves.

The first thing I would do is address the burnout problem

The problem of I am working for someone else and I am really burnt out, this is not something you want to start a company from, ‘cause it’s a hard process.

Starting something really hard isn’t going to solve your burn out. So the first step I think is actually figuring out I need to get into a place where I’m not unhappy, because either becoming an expert or doing the side hustle, having your main job making you really stress out and unhappy, not going to help you succeed on this path.

So, you may need to change your job, you may need to change your habits. Exercise, sleep, how you handle stress. You may need to change things in your personal life, you may need to work on your ability to say no to people and to be able to explain to your manager, “Okay, here’s why I can’t work every night, “and here’s what we’re going to do to solve this problem.”

Because when you start your own company, all these things that stress you out, of all of my customers think their issue is number one, or I have to give someone bad news, or we can’t make this deadline because there’s 18 things about this project you didn’t tell me about, things you will have to constantly deal with, things that are out of your control causing you problems when you work for yourself.

And yes, as someone who works for yourself, you do have the ability to say, “Okay, I don’t want to do this work,” and we’re going to end this relationship with my customer, but it comes with a very clear financial penalty and you have to be able to work through that and you have to be able to work through the things where things don’t work out and we have to start over again without it causing stress and burnout.

The truth is that being your own boss can mean having a terrible boss

You know, my boss doesn’t go away on the weekend. She’s there with me in the morning, she’s there with me late at night, and sometimes, she just won’t shut up about all the stuff she wants me to do and she wants to know why I haven’t gotten it done yet. That is the truth about working for yourself.

So, this thing of being burnt out really is important to solve in order to actually enjoy having your own company. And it may not be something you can solve immediately but it is really worth figuring that out and then, from a more healthy mental space of not being completely burnt out, figure out do I want to go more along this expert route and how am I going to find a small to medium sized company doing something similar to what I’m doing to work at and what is my plan to start trying to find these jobs, start trying to figure out what I can do to work for these folks?

Or, do I want to do more of the side hustle gig and what is my plan to make that actually work in my life so that I can still sleep? So, I can still leave the house occasionally, and so, that I can really not get burnt out again. Really, really tough to figure it out but you absolutely can figure it out.

PSA: Changes in webcasts

I’ve got another question that I’m going to hit up. Before I hit up the question, I do want to just say there have been some changes going on in terms of the webcast that I offer. I no longer offer free signups for my technical webcast. I’m going subscribers only on my technical webcast.

But, there will be lots more Dear SQL DBA podcast episodes. Those are now free and open to everyone. So, in the next one, we’ll be talking about what the deal is with certifications in the next episode, also, do SQL DBAs need college degrees, and lots more stuff. So, I would love it if you can join me for any of the events going forward, but yeah, i have been changing things up.

Choosing your area of focus

Like I said, you have to constantly reinvent things in order to keep things going. So, the question is, “What areas of SQL Server “do you think deserve attention nowadays “and therefore can be an area of expertise for exploration?” That’s a great question and really interesting things when it comes to SQL Server these days. There’s a lot, if you’re at all interested in cloud technologies, there’s a lot of momentum going still for what parts of our applications can we move to the clouds, to the cloud, it really is clouds because we may want to use more than one cloud, we may want to use more than one service, but can we move to the cloud, how much can it save us on cost? And things change rapidly in the cloud. So, becoming an expert on things as they emerge can be worthwhile.

There’s always a risk though that you’re going to learn something new with some new cloud technology that no one’s going to eventually adopt, maybe because it’s just too expensive, right? So, with all of these things, I do think that, yeah, if you’re looking at a new area to specialize in right now, and you want to do consulting and training, the cloud can be really interesting. The cloud is really hard for training though because of the rapid rate that it changes. And I do say if that’s something you’re interested in because I think you really have to like it and be interested in it for it to work. One example of where interest is, and aptitude as well, is really important is things like learning data science.

So yes, learning data science, very, very interesting field, emerging great area for building expertise, but you have to like statistics and math and you have to be willing to kind of stick through it and see where it evolves and learn how what is offered in SQL Server compares to what’s offered elsewhere, right? I know some folks in a college-level course on artificial intelligence who got signed up for this course and, man, apparently it was just a whopper. “This sounds really cool!” And then near the end of the semester, everybody was just like… “This, this is overwhelming!” Like, there’s literally a fire hose pointed at me. So, these areas really are taking off and really are getting a lot of interest, but… Do look at your own… And I don’t love working with statistics, for example, so I will not be going deep down the data science path just because I took a college course on statistics once and I did okay, but I really kind of dreaded doing my homework. It wasn’t something I looked forward to, so, whereas on the other hand, when I first started working with relational databases and queries in SQL Server, I just wanted to work on it all the time.

So, if there’s areas where you’ve got, you know, people say don’t follow your passion. I kind of think that’s BS and I don’t know if it’s really like, “Follow your passion,” but I do think like if there’s things that you find really rewarding to do, if there’s some way you can figure out how to make money at it, even if it’s uncool, even if, you know, it’s not the newest greatest thing, see if you can make money doing that thing. Because you really like working with it and it’s your life! So, you know, I would consider that first, personally.

I mean, if your passion is underwater basket weaving, there are places you can teach that, it turns out. There are ways to make a living out of that.

So, yeah, part of that I would fit into is definitely aptitude, and I mean aptitude, not just as I’m automatically good at it, but aptitude as I’m interested enough in it to keep wanted to do it when it’s really hard because a lot of these things are really hard and we’ll have to keep at ‘em.

It’s really that I like keeping at it and I really want to know it even though it kind of drives me crazy that it’s really hard. I don’t mean aptitude as something that’s just easy.

Thanks for attending or listening to this live podcast session

So thank you, folks, for showing up for this inaugural recorded episode, a live episode of the Dear SQL DBA podcast and thank you for the questions, those are awesome. I hope that you guys have a great day wherever you are and I will be back on April 18th.

I personally am about to head to Hawaii with a bunch of my closest girlfriends, so I’m abandoning the homestead and Jeremiah will stay here while I head off to have some sun and fun with 16 of my favorite women friends, and I will then be back later to do lots more stuff with you guys. So thanks a bunch, have a great day, and I’ll see you soon. Thanks, guys!