Back in December, I wrote about all of the hard lessons I was learning by working for myself. Three months later, many of those challenges have shifted, which warrants a new blog post on the subject. In general, I’ll try not to repeat points from the last post.

So let’s assume that you’ve been working for yourself for 6 months. It’s at this point that one of three things has occurred. 1) You’ve burned up all of your savings and need to go back to a normal job, 2) you are getting enough work to make this sustainable, or 3) you are muddling your way through, making enough to pay the bills, but not enough to be happy.

If you have burned all of your savings it is painful, but you learned something valuable and have clear next steps, i.e. get a job. Consider this like a European gap year. Now you know this isn’t for you.

The barely sustainable path is more dangerous because you might shamble along for 5 years, unhappy and not growing, but too scared to give up your dream. Now is the time to make that hard choice. Step it up or quit.  Don’t wait until 60 months in to decide.

Let’s assume instead that you are doing well, really well. Perhaps too well, even. If you are getting plenty of work, then there are new and very important questions to answer. How do you define work and how do you manage it? How do you decide to “release” work into your enterprise? When do you say no?

If you cannot define, manage and prioritize work within your one-person organization, you will overcommit, incorrectly prioritize and eventually fail. It is as simple as that.  I have been eating a lot of humble pie this month as I’ve had to delay or cancel projects. This is because I planned poorly and overcommitted.

What is different?

So how is work any different than a normal job, and why do we need a better handle on it? So the very first thing is that in a regular job, the work is often more consistent or steady-state. In most cases, the variation in requests each week isn’t huge and so you can predict your overall workload. That workload may be more than you can handle, but you can still predict it.

Spikey workloads

Freelance work, in contrast, is extremely spikey. It’s often called “feast or famine”. There are a number of reasons for this. One is that often you’ll land a big project and the customer wants you to work on it RIGHT NOW. I’m wrapping up a 120 hour Power BI project, and the customer’s ideal would have been for me to complete it all in three weeks. My ideal would be to spread it over 12 weeks. The reality lands somewhere in the middle.

Another reason the work is so spikey is the very long lead times on the sales cycle. Some projects can take 3-6 months from first conversation to the contract being signed. By the time the sale closes, you may have already signed up for other commitments. Even worse, guess when you will have the most time to focus on sales? When your funnel is empty. So you get this ugly sine wave of working a ton on sales, then landing a bunch of work and being too busy to work on sales. Then the cycle repeats.

One other reason for the spikiness is if you are a freelancer, you are likely working alone at first. Which means you can’t take emergency work or that 120 hour project and spread it around as easily.

You control your workload

At my last job, I had very little control over what work got “released” or “approved”. I could prioritize and order my tasks, but I wasn’t the one coming up with them. The bulk of my work was based on requests from customers either internal (co-workers) or external.

As a freelancer, you have the power of saying no. You can fire customers. You may not be in a financial position to do it just yet, but that is one of the goals. Paul Jarvis describes it as being able to have a diva list. You control the conditions of your work.

This is especially true when it comes to non-billable work.Nobody wants to turn away paid work, but it’s totally on you if you decide to sign up to write a book, or start blogging every week, or present to more user groups. And because your workload is so spikey, you may sign up for these things when your workload is in a trough and regret it when work picks up. Which is…exactly the trap I fell into.

Your work is less visible

If I present at a user group, is that work? If I chat with people on Twitter, is that work? If I read a book about marketing, is that work? The answer to all of those is a distinct maybe, it depends. If they are work, then they take up time and they need to be monitored. Otherwise you’ll end up wondering why you aren’t spending more time on paid work.

One of the “click” moments for me was when I mapped out all of my non-billable commitments I had made. On an ideal week, I am spending a FULL DAY of work on things that don’t get me paid. Well, at least not directly. Secretly I hope that you’ll start reading my newsletter, fall in love with me, and watch my paid Pluralsight courses.

This was not a problem at my last job, because I had a standard set of hours that I worked, and when I went home it was my time. Anything I did extra, like blogging, was icing on the cake. Now it’s a lot blurrier. I treat things like blogging or my newsletter as marketing expenses. I consider those things to be “work” and I track my time in Toggl accordingly.

Which reminds me! Are you tracking your time? If not start now. Toggl.com is completely free and has a simple app too. We manage what we measure. Nobody says you have to work 40 hours per week, but you need to make your work visible to you so that it can be managed and controlled.

What can we do?

So, I’ve been wrestling with these issues a lot. Going freelance reminds me of the Foundation series by Isaac Asimov, where a society faces a life threatening crisis, resolves it and then faces a completely different crisis. Managing work is my current crisis. There are two books that I can recommend that have been foundational (no pun intended) for how I relate to work.

Getting Things Done

The first book, which has transformed my work for the past 8 years, is Getting Things Done by David Allen. There is a lot to this book, but it’s all quite practical stuff. It’s the sort of thing that you’ could have invented yourself with enough time and effort. One of the key insights is that David breaks work into 3 main buckets:

1. Pre-defined work
2. Work as it appears
3. Defining your work

Realizing that it’s valuable to spend time predefining your work, giving it a shape, and making it actionable, these are all amazing insights. GTD helps us turn a nebulous cloud of “work” into manageable, actionable tasks.

What is does not do, however, is provide a lot of guidance on managing the capacity, flow and priorities of our work. While it touches on looking at higher level goals, it treats work as a giant refined todo list, filtered by specific contexts. There is nothing in it that says “Hey, maybe don’t sign up to write a book because you might get busy.” For that, our next book comes in to play.

The Phoenix Project

Until very recently, I have never understood Devops. I got the general idea of unit testing, CI/CD and so on. But I never grokked Devops, to understand it in my bones. The Phoenix Project changed all of that , and it changed how I relate to work. Minor spoilers ahead.

In The Phoenix Project, work is defined in 4 different buckets:

1. Business projects. Projects that add value to the bottom line.
2. Internal projects. Projects that improve stability and efficiency.
3. Changes. Sources of risk introduced by the two above.
4. Unplanned work. Break/fix type work.

This ties in to the idea of the billable/nonbillable distinction I spoke about easier, as well as making work visible. As a freelancer, you are a “factory” of one, and you have to understand what commitments, internal and external, that you’ve taken on.

After reading the book, I felt utterly embarrassed, like some plant manager who was drunk on the job releasing work willy-nilly. What I learned from this book is that work in progress is the silent killer of productivity and I was producing tons of it.

Another insight from the book is to ask what are your work centers, a la the theory of constraints. What constrains the types of work you can do and when? In GTD, those constraints are largely physical and contextual: phone, email, computer, office, etc.

But in applying the theory to my own life, I realized a lot of my constraints are brain power and energy. Often I was doing brain-less work, like my newsletter when I was at peak energy, instead of doing my more intensive work, like writing courses. It was revelatory to see the constraints and “work centers” in my own factory of one.

One of the steps that I took to address this was to start capacity planning. I looked at my hours in Toggl, and looked at how much of that time was billable. Then I mapped out the total hours for my current commitments, then divided by the previous number. This helped me assess how many weeks of backlog I had at the time.

Summary

As a freelancer, you have much more control over what work you do or don’t do. But, the definitions for what counts as work get hazier and less visible. You need to take time to resolve that fact, as well as looking at your capacity in whole and over the long term.

I personally still haven’t gotten the hang of this. I look forward to your thoughts and book recommendations in the comments below.

There was a long discussion on Twitter yesterday about whether you should get certifications or not. While the answers were all over the place, there were a number of common refrains. The general consensus was that experience is always better when possible, but that a certification is better than nothing.

This being a complex topic, I thought I’d lay out the various factors to give a more comprehensive answer than you can easily fit in a tweet.

So the first two questions we need to answer are “Why do certs exist?” and “Why do people take them?”. Without these, we can’t give a good answer to whether you should take them. Certifications often exist for reasons that have nothing to do with your personal best interest. It is necessary to understand that fact.

Why do certs exist?

A vendor like Microsoft does not create a certification as an act of charity. Certifications are an expensive thing to create. I wrote all of the questions for the Pluralsight Power BI skill assessment and it was a gruelling process. I was asked to write at a different level of understanding and to try to have plausible distractors as wrong answers.

While they do charge money to take a certification exam, I suspect Pearson takes most of that money and Microsoft likely breaks even, if anything. Oracle, on the other hand, charges quite a bit for their certifications. So we have to ask, why would Microsoft or another vendor create a certification? These driving factors will shape the content inside a certification, so it is important. A few reasons come to mind:

1. Marketing
2. Business/partner relations
3. Technician adoption
4. Market driver

Now it’s worth saying that these reasons apply specifically to a third party vendor. Platform neutral companies like CompTIA are trying to act as an accreditation body and have different motivations.

Marketing

Certifications are a marketing tool. They are a way to highlight new features in a new version of SQL Server, for example. That highlighting is also done out of necessity so that people can’t auto-pass the latest version of a certification.

Additionally, having certifications looks good on a company and is an indicator that the technology is fully-baked. I remember years ago looking into Vertica, a niche columnar database engine way before the time of Power Pivot. I remember looking into getting certified in the technology and thinking “Okay, they are pretty niche, but they have a certification path, so there must be something here.”

The same thing could apply to Microsoft and newer technologies like Power BI. It took a number of years for Microsoft to come out with a certification for that technology, in part because it changes so quickly. I could easily see an IT manager that is considering adopting Power BI using the existence of certifications as a sign that a) there is a path forward and b) Microsoft has made an investment and is unlikely to dump the technology.

Business/partner relations

Businesses need a way to assess the skill level of job applicants as well as growing employees. Certifications, along with college accreditations and years of experience are ways to measure someone’s skill level. Now, certifications aren’t necessarily a good way of measuring skill level. Often they measure memorization skills, certifications can be cheated, and sometimes certifications are out of date with the real world. But they are quick and easy from a business perspective.

At my last job, if I recall correctly, to get to level 2 on the help desk you had to pass the CompTIA A+ exam. This served as a clear bar of entry, and because turnover was so high on the helpdesk, reduced the amount of work assessing the skill of people who were likely to be gone in a year anyway.

Microsoft has a similar problem with Microsoft partners. Microsoft wants as many partners as possible, as long as they are competent and credible. So, how does Microsoft give a partner their stamp of approval without going through and an expensive auditing and assessment process? They use 3 criteria:

1. Social proof. To become a Microsoft partner, you need 3 customers that will vouch for you.
2. Certifications. You are expected to have 1-2 people with certain Microsoft certifications.
3. Capital. You need to pay a certain fee to become a Microsoft partner.

Technician adoption

It is in Microsoft’s best interest for there to be a clear path forward for people to learn their technologies in order to increase technician adoption. If they want technicians to start using Azure, for example, there needs to be a smooth path from remembering to understanding to application.

Certifications represent a small piece of this, along with training materials, Microsoft conferences, evangelists and so on. In theory, certifications represent a stepping stone to becoming an expert in a new technology.

Market Driver

Did you that Microsoft desperately wants you to learn PowerShell? They likely see it as a key differentiator and a way for them to stay relevant in the age of DevOps and infrastructure-as-code. So, let’s say that you are an executive at Microsoft and you want more people to use PowerShell, how do you accomplish this?

Well, one option is to add it as a requirement to many of your IT Ops certifications. And that’s what Microsoft has done. If a vendor has a large enough base of people taking exams, they can drive what people have to learn via the certification requirements.

Why do people take certification exams?

There are two reasons people take certifications:

1. Accreditation
2. Learning a technology

The important question is are they good for either of those?

Accreditation

In terms of accreditation, certifications are a mixed bag and can even be a negative indicator. By definition, the things that are easiest to write for standardized tests for fall near the bottom of Blooms Taxonomy. And so despite a decent variety in the types of questions Microsoft uses, tests are naturally going to cater more toward people who are good at book learning and memorization.

Another issue is that is often easy to cheat on a certification. Testing centers do a good job of watching your conduct and verifying your identity. So in-person fraud isn’t an issue. However, it’s pretty easy to find dumps of the exact questions used on an exam. I once had a co-worker that had accidentally used a dump to study and was asking the team about the right answer on a question. I pointed out to him that that was a verbatim question from the exam I had just taken.

Microsoft is making strides to address these two issues by introducing labs into their new role-based certifications. This will address the roteness and cheating.

Compared to what?

An important piece of this is compared to what. The general consensus was that real, hands-on experience is almost always better than certifications. But for many new to the field, especially if you don’t have a bachelor’s degree it can be a catch-22. You need experience to get a job and you need a job to get experience. Certifications can be a way to break this paradox, along with internships, boot camps, MOOCs, home labs and side projects.

Another issue is if you are settled in a job and want to pivot in another area. For example, let’s say you are a DBA that wants to pivot into Machine Learning. Part of the challenge is you are likely not gaining direct experience in your current position. Getting a certification in machine learning could help show that you have enough knowledge to make that transition.

If you have the option to do an internship or a real project, I would recommend that over getting a certification. But lacking that, a certification is a decent option and much better than nothing. Just be aware that the content can be skewed and not always in line with the latest best practices.

Who is looking at them?

Another thing to consider is who is going to be looking at the fact that you have a certification? As I said, they can be a bit of a mixed bag and I believe that IT managers understand that fact.  However, in many organizations, it isn’t IT who is the first pass but HR. HR, by not being domain experts, are more likely to lean on easy metrics and more likely to value certifications. In a pile of resumes, a certification could be what gets you past the first filter.

Learning Path

The other reason people get certifications is as a way of learning. The general opinion on this is decidedly negative.  Much of this is because of the skew we talked about towards new features and memorization. An ideal certification exam would give you a real problem and force you to solve it with the tooling. The second half of the Microsoft Certified Master was like this and was very well respected. It was also expensive and cost thousands and thousands of dollars to take.

Additionally, if you are just looking to learn, there is a vast set of free and cheap resources to learn. Often times you would be much better off with a technical book and a home lab, just banging away at real-world tasks.

But that being said, I have a much more positive opinion of certification exams. I think a lot about a quote by Donald Rumsefeld:

Reports that say that something hasn’t happened are always interesting to me, because as we know, there are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know.
But there are also unknown unknowns—the ones we don’t know we don’t know. And if one looks throughout the history of our country and other free countries, it is the latter category that tend to be the difficult ones.

When you are just first starting with a technology, it is utterly overwhelming how many moving pieces there are. I find certification invaluable in getting a lay of the land and addressing those unknown unknowns. Certifications can be a way of getting past impostor syndrome and feeling like you understand a technology.

Are certifications skewed and sometimes wrong? Yes, absolutely. But they are also generally comprehensive and touch upon a wide swath of subjects. I think a lot of when I got my second certification, specifically on SQL Administration. I remember reading about high availability and thinking “I don’t need to know this, we have like 2 SQL servers.” Which was true, until I accidentally became a consultant and was configuring mirroring for customers.

Summary

Certifications are a flawed tool, often skewed toward certain subjects, outcomes and types of learning. But despite all of their flaws, they can be a way to get your foot in the door somewhere or get a broader understanding of a technology. They shouldn’t be your first choice, but they shouldn’t be ignored either.

Normally, I’d spend a few hours writing some eloquent 1,000 word blog post, with a dozen sub-headers and very mild puns. Today is not one of those days, as much as I want to make sure I do the topic justice. I’d rather get this written than push it out.

My rickety raft

If you are looking to become an independent consultant for the money, welll I’d advise against it. I wrote before about lessons learned and while you can make a lot of money, it’s a big slog and a big stress. I would compare it to trying to build a big wooden ship, from a rickety raft while you are using the raft.

Only now, about 5 months in, are things stable enough that I can relax. Our finances are solid for the next 3 months and we’ve finally gotten some walls on our raft. It’s still ricketey, but it’s going to take more than any single wave to topple us. It will likely take the rest of the year to get things completely stable.

If I was looking to make more money, the smart move probably would have been to take a job with “Senior” in the title and get a 20k pay bump.

The real benefit

There are a handful of reasons why I made this leap. I was tired of feeling overworked, I wanted to give this a shot, I wanted to work less hours, I wanted to travel more and give more presentations, etc. But a least a third of it, was knowing that in 5 years, or 10 years stuff was going to hit the fan with my mom.

I’m currently the primary caretaker for my mom. She lives independently and gets a lot of services from a Medicare replacement program, called Life Beaver County. I usually describe it as adult daycare meets medical center. They clean her place once a week and have nurses make sure she takes her medicine. For a while, my responsibilities were just grocery shopping every week and occasionally taking her out to go shopping.

But in the back of my mind I knew that as some point those needs were going to escalate. I knew at some point down the road there was going to be a year where she wasn’t well enough to live totally independently but not ill enough to go into assisted living. And very recently, I’ve gotten a, ahem, new commute.

My new commute

Things had escalated recently to the point where I knew that if my mom didn’t get more care, her physical and mental health were going to deteriorate. And so, somewhat reluctantly, I decided to start driving my mom to Life Beaver County every morning.

I am utterly blessed to be able to do so. While it’s a pain to spend 60-90 minutes every morning waking up my mom, getting her ready, taking her in; I am truly lucky to have it as an option. Right now I’m optimistic that her physical and mental health are going to greatly improve and that this could be the difference between being in a home in 10 years instead of 2.

Working for yourself is an utter pain. It requires a whole new set of skills as difficult as learning to be a manager, in my mind. But it also brings some options that just aren’t available with most jobs.