Content warning: burnout, health issues

I have not been looking forward to writing this blog post. I started the series, inspired by Brent Ozar’s series, because being able to see how the other side lived helped me to evaluate the risks and take the leap to work for myself. Unfortunately, that commitment means writing about one of the worst years of my career, and what has felt largely like a waste.

A health scare

2023 started off in a state of burnout, techniques for recovery that worked in the past had stopped working. I was forced to try taking 2 consecutive weeks off for the first time in my career, and it helped dramatically. Also, during this time I was panicking about the change in payments from Pluralsight, and I reached out to everyone I could think of who sold courses or had a big YouTube channel for advice. Thank you to everyone who spent the time to help.

As a result I had decided I was going to start selling my own, self-hosted courses. I think I had hoped that I could just ramp up the social media a smidge, ramp down the consulting a smidge, and make it all work. If I could go back in time, I would have cut down on all extraneous commitments and focused just on this. Instead, I tried to make it all work, because of what I thought I “should” be able to accomplish, or what I had been able to accomplish in years past.

Around this same time, Meagan Longoria (along with others) convinced me at SQLBits to raise my consulting rates by 30%. Meagan has the tendency to be painfully blunt, while also being kind and empathetic. I think it’s difficult to nail both candor and kindness at the same time.

The health scare came in March, when I started weighing myself again. Travel from Bits and work had caused me to fall out of habit with exercising. What I found was I was the heaviest I had been in my entire life at 300 lbs. Even heavier than when I was in college and considered myself fairly obese. I had gained 20 lbs in 3 months, which as a diabetic is very very bad.

Barreling towards burnout

I decided I needed to do something, so I bribed myself with a Magic the Gathering booster every morning I exercised, and a Steam Deck if I could do that daily for 3 consecutive months. Overall, that worked, but I did find that in my mid 30s, it’s hard to just push through like that. I have to be careful, or I’ll develop plantar fasciitis or some other issues for a while.

At the same time, however, my work requirements had picked up. I had signed up for a volunteer position with a local organization that had become very stressful. I had work projects that had dragged on longer than they should and were starting to frustrate my customers. And I had found that the branding and marketing of selling my own courses involved much much more work and executive function than I had realized.

I did end up contracting and then hiring part time a local college grad to be my marketing assistant. She was recommended via a close professor friend of mine and overall she has been great. The biggest challenge has been acclimating someone to our particular niche of the data space and what the community is like.

Around June, I realized I was simply spread too thin. I had experienced being physically unable to get out of bed any sooner than was physically necessary. I was physically unable to get up an hour early for work to try to push through a project or deadline. I was should-ing myself to death, taking on more than I could handle because I thought I should be able to do more, because I thought people would be disappointed in me if I had to close out projects and work.

Ultimately, the largest threat to my health and well-being was my own personal pride.

Turning the corner

Thankfully I did decide to wind down as much of my consulting work as I could. It took multiple months longer than I would have preferred, honestly. I closed out any open projects that I could easily do so, and now I’m down to 2 customers that are a few hours per week. I also decided that I wouldn’t take on any new projects during November or December.

I’ve also been focusing on making that course and I officially have given myself a hard deadline of February 5^th. At the moment I have absolutely no idea how well it will do. If it does well, that means I can continue to focus on making training content for a living. If not, I’ll have to consider pivoting into more of a focus on consulting or going back to a regular job. I would have preferred to be releasing this in the summer of 2023, but here we are.

I think the hardest thing to grapple with regarding burnout, is the uncertainty of how long it will take to recover and how aggressive you have to be in resting to recover. I’m grateful to both Matthew Roche and Cathrine Wilhelmsen for putting that into perspective.

There are days that I feel much better, I feel energetic and enthusiastic. Coming back from PASS Summit, I felt that way all week. But at the moment it’s still fragile, and I have to remind myself that a good day in a week doesn’t mean the issue has been totally solved yet.

One other thing, I always struggle with the lack of sunlight in the winter. For the first time ever, I’m being proactive about it and going somewhere warm in December instead of January or February when the issue becomes apparent. So, I’ll be spending Christmas week in San Juan, Puerto Rico where it is currently 80 degrees Fahrenheit. See y’all on the other side of 2024.

2022 was my best year financially and probably my worst year personally. This was the year that we achieved financial independence. We had 6-12 months of expenses in the bank and the royalties were covering our living expenses. It was also the year that I found that a relaxing weekend off wasn’t enough any more, that bouncing back wasn’t working anymore.

Too much, all at once

2021 was very quiet year as far as my consulting was concerned, about 10% of my revenue was consulting and the other 90% was royalties and completion payments. In 2022 that changed, however.

There was about 3 months where I was billing 20-30 hours per week on top of signing up for a new course near the end of it. Because the royalties were covering my expenses, this all went right into savings and we ended up with 6-12 months of savings. This is a consultant’s dream.

Unfortunately, life was occurring at the same time.

My husband had an elective surgery that we were planning for months. It went great and he’s completely recovered. What this meant, though, is that I was tasked as nurse for 2 weeks and janitor for 3 months. I was suddenly doing all the chores that I had taken for granted, while also working 40-50 hours per week.

Near the end of this my mom started having issues as well. The isolation of Covid was finally taking it’s toll and she was having more issues. She was clearly lonely and bored and only really got out of her apartment every other week.

This also has been largely resolved, but for a while I was bribing myself with Magic the Gathering boosters to call her every day and check up on her. We’ve increased the services that she’s receiving, and she gets out twice a week now, but during the summer it was a really challenging time.

When your body stops working

I think many would describe what I went through as burnout. I’m not sure of the right term, but stuff just stopped working. More coffee didn’t help. I would schedule a weekend to catch up on a course and get nothing done. I would take a few extra days off, to no lasting effect.

Something broke.

Realizing I needed something more, I schedule 2 weeks off at the end of the year. As a consultant it’s difficult to take time off unless you plan it far in advance. It’s even more difficult if you feel like you are always behind on projects. I only made 2 courses this year and the second one was 3 months late, horrifically overdue.

I’m one week in and I think this was 100% the right choice, I needed a deeper rest to catch up from the last 3 years.

A gut punch from Pluralsight

A couple of years ago, Pluralsight was purchased by private equity. I was cautiously optimistic at the time that this might enable them to get away from the quarterly cycle of the stock market. The results were mixed, with them making a very large acquisition of A Cloud Guru, which is still resolving.

But in December this year, the company had 20% layoffs essentially firing 400 employees. There were also changes for authors, and while I can’t get into the details, I’m expecting my royalties to go down 25%. This will put me below sustainability, with royalties no longer covering 100% of my living expenses.

So now what

For now I’ve been focusing on enjoying my vacation, recovering from 2022, and not worrying about the short term. I’ve also been reaching out to colleagues and peers, asking for advice.

I no longer see PS as a sustainable career, which means looking into doing more consulting or selling my content elsewhere. I could also get a regular W-2 job, but I would lose much of the flexibility that helps me take care of my mom.

In the end, I think I’ll be fine. But I have no idea what I’ll be doing for a living by the end of 2023.

This month marks my 3 year anniversary of working for myself. I think it was undoubtedly the right decision, but it doesn’t quite feel firm and real. Here are some lessons learned as I enter my third year.

Learn how to work, or fail

I think the hardest lesson for me is that the biggest challenge has not been the technical piece. I know how to do that, and I’d like to think I do it well. I even have somewhat of a grasp on the sales and marketing piece. The hardest part is the daily art of working.

I’ve said it many times before, but there is so much scaffolding that comes from having a workplace, co-workers, and a boss telling you what to do. You expect to just be able to get stuff done when you work for yourself, and that’s just not the case. It’s frustratingly difficult.

In reality, there is a whole suite of skills that need to be learned to work for yourself, to work from home, etc. for example:

1. Switching between strategy and execution
2. Setting boundaries at home
3. Scheduling work
4. Identifying what’s profitable and drives the business forward
5. Tolerating financial and career uncertainty

My biggest regret has been not focusing on these things from day one. My biggest struggle right now is the art of daily working and daily success.

Invest in your environment

Related to that, in the last 5 months, my royalties have been at an all time high. That this feels real and stable, and has caused me to reinvest in my environment. I think that is also something I wish I had done earlier.

When I first started, I was using the same laptop for both leisure and work, and this quickly lead to a poor work-life balance and everything feeling like a blur. For the longest time I used a $100 desk from Staples.

More recently, I purchased a standing desk and it has been wonderful. I bought three 27″ monitors. I bought a streamdeck and use it for time tracking launching applications. I purchased $400 headphones, which feels utterly decadent. But I’m realizing it’s all worth it.

Ultimately, not investing in my environment for so long is a kind of stubbornness. I keep expecting to just be able to work, but this depends on some reservoir of willpower and focus, which is always more limited that I expect. Too often I indulge in “should” thinking.

How much money do you need?

One thing that has been a point of frustration is that my top line revenue for the past 3 years has been fairly flat. And sometimes I wonder if I’ve made a mistake. But just looking at top line revenue doesn’t tell the whole story.

First, if you look at where that revenue came from, there’s been a huge shift over time. That first year, 80% of my income was consulting and 20% was royalties. And much of that consulting was work I didn’t want to do, but did to pay the bills. By year three, that ratio has flipped. Covid tanked a lot of consulting but doubled my viewership.

One big benefit of that is now my income, while not higher, has become more stable and predictable. Not once during the pandemic did we have to worry about paying the mortgage. In contrast, I know a couple consultant friends who had to go back to getting a job.

Another benefit has been supreme flexibility. It comes with frustrations, as mentioned above, but I’ve been able to just take a day off, whenever I want. I can take my mom to a bird fair, and it’s fine. I think a lot about folks who get promoted, make an extra $20k but are working 50 hours per week and are miserable. I try to remind myself that I’ve take the reverse choice.

So what’s next?

I plan to continue doing consulting on Power BI and the Azure data platform. I think it’s essential as an instructor to stay grounded and relevant. And I enjoy it! But I’m accepting that my main job is to be a perpetual newbie, having to constantly learn technology and package it up for others. This means focusing on instructional design and, more importantly, how to get work done on a daily basis.

In the short term, I’m working on 3 Power BI courses for Q4 and then hopefully taking the last 6 weeks off for 2021!

Two years ago I quit my job and started working for myself. After two years, I think most people would look at it as a big success, I’m now finally able to make a stable living doing what I want. As we enter a recession, I know a lot of people would be grateful to be in my position.

But I’m also vaguely dissatisfied, because the past two years have have been an unfocused 24 months, running around putting out fires and trying to pay the bills. After 4 years of work, Pluralsight revenue pays a reasonable salary and I can take a peaceful vacation. When I come back from my cabin trip next week, I’m hoping to have a better idea of what the next 4 years will look like.

Four years from idea to full-time income

Four years ago, a friend convinced me to think bigger and in March 2016 I applied to be a Pluralsight author. I have never spoken at any large conference, I didn’t have any impressive credentials, and I didn’t expect to be accepted. But it turns out the hard part isn’t getting your foot in the door, but getting your audition approved. Imagine doing a recorded lightning talk that has to convey a technical concept but also tells a story.

It took about a year to go from starting the audition to getting my first course being published. A lot of this was delays from underestimating just how difficult it would be to make my first course, taking 140 hours plus some outsourced editing. All of this was during nights and weekends while working a full time job.

The chart above is the 3 years it took to go from first course to full-time income. And while I can’t share exact numbers I’ve got two dotted lines there. The first one, in grey, is the bare minimum I would need to make, in addition to my husband’s income, to cover our minimum expenses. This includes paying $900 per month for our own health insurance.

The green dotted line is what I’d need to make to cover our expenses and live comfortably here in the Greater Pittsburgh Area. Additionally each orange dot is a new course being published. I’ve also labeled when I went part time, when I quit my job, when the Power BI learning path came out (with 5 of my courses in it), and the Free April promotion that brought in a lot of new users.

Two years of juggling and struggling

I think one of the key takeaways from the chart above is it took nearly a year of working for myself before my courses could cover by base expenses, and another 8 months before I could finally breathe and not worry where my next paycheck was coming from. During that time, I was trying to do consulting jobs to pay the bills, while completing the next course.

The whole of is chart is punctuated by moments of luck and risk. I was lucky that my second course, on DAX, was enough of a hit that I was about to go part time. It was a big risk quitting my job, since it took a year to get somewhere stable. Both times I hit one of those financial goals were because of an external event. The first was the release of the Power BI learning path, which increased viewership. The second was the FreeApril promotion, which brought in a lot of new viewers, many of which wanted to learn about Power BI.

Success comes from rhythm and routine

The reason I feel dissatisfied is that success comes from rhythm and routine. When you work for yourself, you are the only person rowing. You are the only person blogging, speaking, marketing, etc. And either you find a weekly routine that keeps you going through the difficult times or you will struggle and have moments of no momentum.

In retrospect, trying to do consulting and content creation at the same time has been a great way to diversify my income. As we enter a recession, I see the consulting work drying up and at least one friend going back into regular employment. But it has been challenging balancing the two. Consulting work is all hurry up and wait. Content creation is a slow and steady focus. The two always seem to be in conflict.

I never quite hit a solid rhythm and with Coronavirus happening, all of my extracurricular activities have stopped. No newsletter, no blogging, no presenting. I think this has happened to a lot of people, and I admire the folks who have been putting out weekly content during a global pandemic. When I come back from my vacation, my biggest priority is starting up a new rhythm.

Would I do it again?

I would absolutely do it all over. I wish I had been smarter about some things, but the hard part is over. I don’t need to worry about being fired, or losing my job during a recession. I’ve been able to visit my mom three days a week without worrying about an angry boss or work conflicts.

So am I going to keep consulting? Yes! I think that being a full-time author runs the risk of losing touch with the technology and where things are going. Consulting forces you to be grounded. I think doing a blend is great when you can do it, and awful when you are still figuring it out.

In my experience , working for yourself provides a unique set of challenges and required skills. You need to learn how to work on your business, not just in your business. You have to become your marketing, sales and HR departments. Without useful resources, I undoubtedly would have failed as a freelancer. Below is a list of resources I would recommend to anyone getting started as a freelancer.

Blog posts

As I’ve made the leap to working for myself, I’ve written a set of “lessons learned” posts.

• 3 months in – Managing time and revenue
• Are your your business? – Could you sell your business?
• 6 months in – Managing your workload
• 12 months in – Rebuilding structure

Podcasts

Podcasts are my most valuable resource, because they provide a slow drip of insight and expertise. Listening to a podcast provides a regular insight on how other think about this stuff, without a large commitment.

• Business of Authority. This is my #1 recommendation in podcasts. Rochelle and John are focused and understandable. This isn’t some 2 hour rambling podcast. They provide expertise from very different types of businesses. Every week I enjoy listening to this.
• Ditching Hourly. John continually beats the drum of “hourly work is bad”. Even if you never switch to a flat-rate model, this podcast will help you think of yourself as a business, not as a technician.
• Startups for the Rest of Us. While the topic is startups, the actual focus is small businesses. If you are a business, this podcast will have something for you.
• The Freelancer’s Show. More of a casual chat format, this show regularly has lived experiences from developers working for themselves.
• Finish your Damn Course. If you are a freelancer, you should consider offering products, not just services. Janelle interviews a wide variety of guest who are making training courses on wildly different subjects.
• Creative Class. This podcast is generally only active when the Creative Class course is open for enrollment. I love the easy style Kaleigh and Paul have when talking about freelancing.
• Building a Story Brand. Marketing isn’t always fun or intuitive work, but it is important. Donald Miller explains marketing in wonderful down to earth terms.

Books

Sometimes you need to read a book to get a core idea to stick. Many of these books are also available as audio books, so even if you are busy you can listen to them while exercising or cleaning.

• • Consulting

• • • Getting Started in Consulting. If you travel, you probably have a checklist of everything to pack. This book is a big checklist of everything for starting your consulting business.
    • The Secrets of Consulting. Consulting is the art of telling people they are wrong without them having to admit it. This is a fun read on all the weirdness of being a consultant.

• Running a business
  • The E-Myth. So many of us go freelance because we are great technicians. But we also have to be managers and entrepreneurs, and much as we might hate it. This book covers that through a great parable.Company of One. I absolutely love Paul’s approach to running your own company. This is a great book for thinking about the unique advantage of running a company of one.
  • Building a Story Brand. If you buy one book on marketing, buy this. It is the most intuitive, plain-English explanation of what marketing is that I have ever seen.
  • Built to Sell. While it’s almost impossible to sell a one person business, it’s important to think about it anyway. Much of your work can be automated or outsources, but you have to work hard to identify which parts.
• Productivity
  • Getting Things Done. The best book I ever read on productivity. A series of simple guidelines for defining and organizing your work.
  • Atomic Habits. One of the hardest parts of working for myself was rebuilding structure and routine. This is a great book on the subject, very practical.
  • The Phoenix Project. While technically a book about IT management, there is insight for everyone. I found this book tremendous in helping me think of work as a flow and not just concrete tasks.
• Communication
  • Crucial Conversations. While few customer conversations get heated, this book has clear advice on reaching agreement sooner and deescalating critical conversations.
  • How to Have Confidence and Power in Dealing with People. The name is a mouthful, but the book is pure gold. This books is how I learned to make small courtesies and always paraphrase back what the customer says

Courses

I’ve only taken one course for freelancing and the was the Creative Class course by Kaleigh and Paul Jarvis. If you are brand new to freelancing, I would consider this but definitely listen to their podcast before you buy. The content is easy to follow and enjoyable, but quite introductory. If you’ve been doing this a year or more, you likely won’t get as much value out of this course.

Software

There are tons of pieces of software out there for running a business, but here are some I have had experience with.

• Toggl. I use toggle to track my time spent. Having a weekly timesheet makes it easy to track billable hours and review what my focus is.
• Trello. If you need to collaborate or track todos, Trello is a great free tool.
• Quickbooks. If you are running a business, then you need to track your books and send invoices.
• Mailchimp. I send my weekly newsletter using Mailchimp. It’s simple to use and fairly cheap to start out.
• Buffer. whenever I have a presentation or a course coming up, I like to schedule social media posts. For that, I use buffer.
• Emergent Task Planner. Not actually software, but I find this note pad to be useful for planning and tracking my day.

Summary

When you work for yourself, you need to manage the entire pipeline Marketing –> Sales –> Delivery. You need to think of yourself as a business, and you need to have a plan for growing your business even if you always stay a “Company of One”. You need to rebuild structure and routine and find a way to focus on your work.

Consulting is a unique job. Freelancing is a unique job. With the right resources you can succeed at both.

This months marks one year of working for myself, and undoubtedly I feel mixed about it. I’ve made a number of mistakes that I can’t help feeling dumb about. In retrospect, I probably wasted three months learning these lessons the hard way. And yet, it’s a lot like a hot stove. People can tell you it’s hot, but until you touch it you won’t quite grasp it. Here is what I’ve learned from a year of self-employment

What I learned

Don’t force your job into your dream job

When I quit my job, I had ambitions of doing all the things that give me life. I was going to attend more conferences. I was going to study all of the time. I was going to write more. I would work whatever hours I wanted, whenever I wanted. These were all things I imagined I would do once I quit my job.

And while I did many of these things, I was putting the cart before the horse. What I learned is that I needed to get the fundamentals in place first. I had to learn how work from home. I had to learn how to rebuild the boundaries and structure of a normal job. I had to learn how to create a new routine.

And as a result, I probably spent the first two months a bit unfocused. I also made a number of commitments that I am finally coming out the other side of. While I’m proud of all the presenting and speaking I’ve done this year, I wish that I had put first things first.

Respect your human fragility

I underestimated just how human I am and how hard this would be. Often it was dumb stuff, like needing to set office hours. I’m used to just being productive, just getting things done. But in reality, there was so much invisible scaffolding that had been supporting me, that I had interpreted as my own strength.

When you have a day job, you often have set working hours. You have coworkers and expectations. Consequences are often direct and measurable. Most people work in a different environment than they live in, so our brains have context clues.

All of this goes out the window when you work for yourself and work from home. Consequences are both diffuse and existential. No one will yell at you if you put off marketing or sales, and yet your whole life depends on it. There’s a vagueness there that is unsettling. The temptation is to just work harder, to push harder if things aren’t working. But without some structure to push off against, it is exhausting.

Find a way to rebuild that structure

Through trial and error, I found a way to rebuild the structure I had given up. I set office hours of 9AM-6PM, with an hour lunch. I peppered exercise through the day. I worked on breaking things into concrete tasks. I started building a python app to track personal todos and basic things like checking my blood sugar.

I feel like I’m starting to get the hang of it, but I’m not quite there. I find mixing consulting work with creative work to be a challenge. It reminds me of Paul Graham’s essay on Manager’s schedules versus Maker’s schedules.

The contrast of urgency and distant deadlines, of deep work and quick meetings, can be quite jarring. In theory I’d like to have dedicated days for creative work, but it never seems to quite work.

Join a peer group

One of the smartest things I did during this process was a lucky accident. I was friends with a wonderful peer in the Pluralsight space. He lived near me and was a full time author. And when I quit, he invited me to join his mastermind group. We have a Slack chat and we have a Skype call every other week.

Working for yourself is incredibly and brutally lonely, and alienating. You are making all of these decisions and going through new experiences. Having someone to bounce ideas off of is critical. It is so relieving to have a group of peers going through the same thing.

Take a vacation

Schedule a vacation. Make it happen. It took me 8 months but I had a real vacation. By planning it far in advance, I could warn clients and build it into my schedule.

When you work for yourself, there is a creeping sense of opportunity cost. Let’s say your billable rate is $100. That means every movie is $200 you could be earning. That board game is $100 you could have made. And that vacation is $2,000 you didn’t bill someone.

And that is why you need set office hours. That’s why your need strong boundaries. And that’s why you need to schedule a  vacation. Because otherwise there is a temptation to work yourself into the ground.

Was it worth it?

So, was it worth it? Would I do it again? Let’s look at it financially first.

Financial benefits

At my prior job, I made about $65,000. This year I made $85,000 in gross revenue. So, big improvement right? Well…

So, when you work for yourself you have to pay all of your own health insurance, 401k and vacation. You also have to pay both halves of the payroll taxes. Realistically, it turns out to be a bit of a wash, when you factor in all of these costs. Overall, it has been a modest improvement, at the cost of monthly consistency.

If I really wanted to make more money, I could have taken a job with “Senior” in the title and gotten paid $80-$100k AND benefits. At the same time, It probably would involve being on call or quite a bit of stress.

Personal benefits

The personal benefits are huge, and I will probably not take a regular job for the next ten years. When you work for yourself, you decide what you want to focus on and specialize in. You do set your own hours and eventually you can fire your worst clients. There really is something soothing in knowing you have control over your career.

But beyond that, working for myself has allowed me to be a caretaker for my mother. I’m able to visit her 3 days a week and take her in to a Medicare replacement program. I’ve been able to see a marked improvement in her quality of life as a result.

So yes, it was worth it and I would do it again. I just wish I had a time machine so I could do the first year the easy way, haha.

In Pennsylvania, if you start a business it starts out as a sole proprietorship. Legally, your business has the same name as you, and until you get an EIN, it can be identified by your social security number. In a very real sense, your fledgling business is you. But the question is, should it be?

I recently read two books that have got me thinking about that question. First is “The E-Myth” by Michael E. Gerber, which breaks people down into 3 contradictory personalities: the entrepreneur, the technician and the manager. Whenever you start a business, there is a little bit of each in you. Often times, however, you are mostly a technician. You quit your job because you were good at doing the work. But as I learned the hard way, there is more to running a business than just being technically proficient.

Another thing that it talks about is how businesses should be designed like the prototype for a franchise model. There should be standard operating procedures, code and processes for everything. Literally everything. As a solopreneur, this seems so strange at first.

We get even stranger when we get into “Built to Sell” by John Warrillow. This book is all about making a business that can be sold and live without you. What are the things that make a business appealing to buyers? I say this is strange because, as a consultant, if I left the business there wouldn’t be anything left. It literally has the same name as me, right?

But I’ve been thinking about it more, and not everything has to or should be me. When I make video courses, I pay an editor to do all of the video editing. As a consultant, in theory, I can make anywhere from $100-$200 per hour for what I do. Most of the things I do, such as accounting, or social media management, are nearly as valuable. So logically, even if I can’t separate myself from my business, or ever sell it, I should be thinking about the piece I can carve off. I may be at the core of my business, but I don’t have to be all of it.

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.