Stories about Software


A Slice of My Life: What I Do, Why I Have Money, and How It All Works

It occurs to me that I spend a good bit of time weaving narrative into my posts.  I tell personal anecdotes to ground stories, and I add in a good bit of figurative language.  But it’s always fairly superficial.  I don’t generally get heavily into my own story.  As an introvert, this makes sense, since talking extensively about myself or receiving compliments feels awkward.

But I’ve received a number of requests over the years like today’s reader questions.  So today, for reader question Monday, I’ll talk about this subject.  Here’s the reader question.

I’m interested in how you’d describe what a week, month or a single engagement in your shoes is like. I know a couple of people who are consultants and see them going out to coffee shops, meeting with clients to socialize and making pretty good money. I’d like to read an article about what your routine is like. Nothing where you give away client specifics or anything. I just think others who read your blog are taking in what you write about, putting what they find is useful into practice but are left wondering in their head ‘I wonder what work is like for Erik?’.

Before I dive in, it’s worth noting a couple of things.  First, I have to address this at different times because my life has changed a lot.  And, secondly, it really depends on what kind of consultant you are, so I’ll speak a bit to experiences other than mine as well.

I’m predicting a fairly long post on this one, so buckle up.  I’ve always found that it’s the absolute most difficult to be brief when I’m trying to explain myself, as if I’m constantly mounting a legal defense or something.  Anyway, here we go.

Modern, Reclusive Erik, A Day in the Life

For the last six months, most of my days look pretty similar, weekday or weekend.  I usually wake up around 9 and shuffle to the kitchen for some coffee, preparing to sit at my computer.  Morning time is usually writing time.  This isn’t for my personal edification or for my books, but for my growing content marketing business.  That typically carries me through lunch and a little after.

In the afternoon, I’ll spend some time handling emails, corresponding with clients, and working on the businesses, but that usually stops at some point.  For the last six months, I’ve been living in a house on a lake, featuring usually great weather, great scenery, and generally great marrow waiting to be sucked out of life.  So I go outside.  I jog, I kayak, I do a bit of yard work, I fish, or I make a fire in the fire pit and just enjoy my surroundings.  The weather is getting a little suspect for that here in late October, but we’re getting ready to head south for the winter.  So I expect this routine to continue.

After enjoying life a bit, I eat dinner and then either call it a day or go back to work, depending on how I feel.  This is typically non-writing “deep work.”  Minimal distractions after 8 PM, so I can get in a solid block of concentration until I go to bed around 2 or 3 AM.  Sometimes I also write during this time window.  Other times, I’ll work on software for my codebase assessment practice or my own longer form content marketing.

Why Does This Matter?

You’ll notice what I don’t really talk much about here: consulting.

That’s because I don’t honestly do much of it anymore.  And that’s by design.  I have engineered and hacked my life deliberately and specifically to look like this.

When I do consult these days, the clients seek me out, and I agree only after a heavy round of disqualification.

  • Is it a short term engagement (a few weeks or less)?
  • Will it pay enough really to be worth it?
  • Can I do it from anywhere?
  • Is it a high value, high leverage engagement for the client?

A “no” to any of these questions and many more results in a “no thanks” from me.

I give you this vision of my life, mostly “retired” from serial consulting in order to set the stage for the rest of the post.  Consulting is fun, rewarding, interesting, and lucrative when you do it well.  But it’s also a treadmill unless you specifically make it not one.  It’s the career equivalent of an interest only loan unless you’re careful.

The Life of an Agency “Consultant”

Since most of my readers are software developers, I’ll talk about the different flavors of consulting in that field.  I’ll even discuss ones that fall under this heading only because the software world has a bemusingly wide array of people that it calls consultant.

So let’s start with the agency staff “consultant.”  But we won’t spend much time here, because there’s not much to say.

I had a gig like this once, briefly.  You work for a custom app dev shop, and they call you a “consultant” only because you write software for someone other than the firm that writes your paychecks.  You don’t go to your client company, and you might not even visit the client at all.  The client’s people give your project manager specs, the project manger gives you those specs, and you translate them into code, like some kind of human UML compiler.  I proposed that we call these people “software pros” instead of consultants, because that’s a better term.  There’s no consulting to speak of.

What’s life like for the agency app dev “consultant?”  Just like your life as a workaday programmer.  You might have, on average, slightly more variety in the types of apps you work on.

The Staff Augmentation “Consultant”

Here’s another one not worth spending a ton of time.  This is where, unlike the in-house, software pro “consultant,” you go to the client’s site and write code there for the client.

This one has face time with a client.  So, in a small way, you’re a little closer to actually consulting, but it’s kind of a rounding error.  Categorically, clients pay consultants for advice and expert opinions and not for labor.  If you show up primarily to write code or to, in any other way, join in with the client’s staff in executing anything, you’re a staff augmentation.

What’s that life like?  Well, I’ve never really lived this directly, but I’ve been surrounded by it for more years and projects than I can count.  Mostly, it’s like the software pro’s life and the employee’s life.  You more or less become an employee of your client’s.  Their culture is your culture.

There is one weird difference here, though.  Think of movies about undercover cops on long term assignments, like Donnie Brasco.  You mostly operate as if you were an employee of your client.  But, every now and then, in a reality-inverting and surreal episode, your “real” handler pulls you out into a monthly all hands or a one-on-one.  So this consultant’s life is like normal corporate life, but with a second set of bosses that have somewhat different interests than their day to day bosses.

Actual Consultants at Actual Consulting Firms

Alright, now we’re getting more into the meat of it.  In the software world, just about everyone seems to consider themselves consultants, but there are large firms that actually do deploy consultants.  Price Waterhouse Cooper (PWC) and Deloite come to mind, among others.

You hire these firms to supply you with consultants who do what consultants traditionally do: consult.  Do you need a roadmap or a project plan?  Do you need some expertise about whether you should go with a COTS solution or build your own internal operations management stuff?  Thinking of hiring for a role you don’t know how to evaluate?  You get the idea.

I’ve never worked for a consulting firm like this.  But I can give you a sense of what it’s probably like, based on a gig I had once more than a decade ago.

My Approximation of Firm Life

Back then, I worked as a software developer for a company that, among other things, made mail sorting equipment.  I knew the controller software systems for these sorters pretty well, and I was also the lead developer for an ancillary accounting package for sorting shops.

As a result, I spent a lot of time going out to client sites with specific, targeted goals.  I did the software piece for certain sorter upgrades, and I installed the accounting package and helped train staff on it.  This was execution, so I was clearly not purely a consultant.  But my travel schedule and the targeted, expert/specialist nature of my work approximated consulting.

This is where I first got a taste of the phased life of the true (staff) consultant.

  • Presales, acquisition, and discovery.
  • Engagement
  • Post-engagement retrospective/evaluation
  • Retainer, operations/intellectual property refinement

Life varied a lot depending on the stage.  The reader question mentioned coffee — that’s going to be presales and discovery, most likely.  You meet and get to know clients, discuss how to work together and then plan the engagement.  (I’ll get to SOWs and contracts in a bit — staff consultants wouldn’t worry about this much).

Then there’s the engagement.  Dress like the client dresses (but not nicer, if you ask me), keep the client’s hours, carry yourself calmly and represent well.  Help them out.

After the engagement, you’ll invariably have some loose ends to tie up, some debriefing and the like.  This is where you figure out how to improve.

And, finally, you have “the rest.”  The client will go into sustaining mode, perhaps with some kind of retainer or planned future engagement.  You gear up for your next discovery and, while you wait, you make your offering better, incorporating the lessons of the post mortem.

A Local Free Agent Consultant

Now we’re getting back into what I know and what I’ve done.  My career path involved software development, leadership positions at corporations, and then an exit from CIO to free agent.  Since I moonlighted for years before going full time independent, I’ve actually been consulting now for something like 7 years.  Wow.

I’m going to leave the travel portion out for now, because the free agent part already introduces enough complexity.  So assume you live somewhere, and you’re on your own, serving local clients.  What’s that like?

Well, you have the same conceptual four phases as above.  But you don’t have a firm to rely upon, so they blend together a lot more, and you do more things during each of them.  And you’re a one person show for the business, so you also have to weave in other concerns, like marketing and finance.  Here’s my life as a free agent (omitting the travel).

Week to Week as an Independent Consultant

If you have no prospects, starting from scratch, you’re going to be in “operations” mode.  This means that you’re sitting at home, thinking, “how can I get business, and what should I offer?”  If you’re not careful, you can thrash around a lot, updating your website one day, spewing cold outreach emails like a spam geyser the next.  But however you approach it, you’re looking for business.  You do things like these.

  • Email people you know.
  • Have “networking” meetings for coffee.
  • Write blog posts, speak at conferences, put on webinars.
  • Update your website

Sooner or later, all of this pays off, and you land a gig.  Nice!  You’ll spend some time going through the contract/SOW process (continuing with the operations stuff in the meantime), and then go into discovery and pre-sales.  Usually, your focus shifts to be fairly exclusive to the client at this point.  Wanting to impress, you pour effort into doing this, taking initial meetings and preparing agendas and such.

Once the engagement starts, your life actually starts to resemble normal employment.  You sync up with the client’s business hours, go to meetings, and work there.  Depending on the scope of your work, this could last days weeks, or even months.  (Though if it’s months, that starts to feel more like execution.)  At night, though, you continue operations mode, keeping the lights on and trying to line up future gigs.

As you get ready to wrap, you’ll probably start to fluidly transition into both post mortem mode and ramped up operations mode.  This holds doubly true if you haven’t booked more business yet.  The post mortem, if you’re not booked, will start to turn into a secondary sales “how can we work more together?”

Adding Travel to the Mix

I’ve described this life professionally so far, but I’ll add the personal element to it as well, by talking travel.  Despite living for a long time in a client-rich area, I’ve always wound up doing a lot of travel for engagements.  I have consulting clients all over the US.

Everything I’ve said above applies, but there’s an additional logistics component.  Discovery more frequently happens over the phone, since, absent a signed contract, you’d be handling pre-sales travel as an operational, out of pocket cost.  And you make sure to negotiate the cost of travel when creating proposals and statements of work.  (I prefer to just include travel in my bill rate, removing any potential for haggling with clients over whether it’s reasonable to eat at a certain restaurant or use a certain rental car company).

Travel happens weekly, usually.  This has generally meant Sunday night flights and Friday afternoon flights.  So, during an engagement, I leave for the airport Sunday afternoon and return home Friday night.  I conduct my consulting business operations from a (usually upgraded) room at the Marriott during the week.  This actually works well because there’s not much to do at hotels, so you don’t feel like you’re missing out on life when you work all evening.  If the location is new to me, I’ll explore a little, but mostly you’re going to repeat places.

Eventually, I even stopped going home very much.  Week after week of commuter travel makes home a memory anyway, and if you can avoid the hassle, you do.  I’ve live out of a suitcase for years, working 60 hour weeks from client sites and rooms in Marriotts.

The Four Seasons of Consulting

I’ll talk shortly about my experience in more narrative, personal detail.  But 2400 words in, it’s time to take a breath and examine what all of this means.

For the solo consultant, you have the four “seasons” that I’ve covered:

  • Pre-sales/acquisition.
  • Engagement
  • Engagement wrap/post-engagement
  • Operations/business

A day or week in the life of a consultant is as different as yours might be during one of the four season of the year.  And there’s even more variance than that, because different consultants distribute their time differently among these seasons.

For instance, consider the siren song of long term contracting.  Serially looking for business can be really time consuming and painful.  So some consultants respond by digging into their clients like ticks and staying there indefinitely, becoming de facto contractors.  Other consultants, particularly financially independent ones, might spend the overwhelming majority of their time in operations mode, honing their crafts and expertise.

It really varies.  So with that in mind, let’s really get into my consulting story.

My Consulting Origin Story: Confessions of a Naive Malcontent

As I’ve discussed in Developer Hegemony, I became a free agent consultant by default, in a sense.  After years in the workforce as a software engineer, architect, manager, and then CIO, I concluded that I grew disillusioned with jobs too quickly, thoroughly, and inevitably to have one.  So, rather than change jobs all the time, I went solo.

It wasn’t as completely impetuous as it sounds.  I had consulted and contracted in a moonlighting capacity.  I did have some Pluralsight courses to my name and a blog with some following for lead generation.  But I neither fully understood the implications of those things, nor did I explicitly capitalize on them initially.  I turned my last employer into my first big, solo freelance client, and struck out on my own.

At first, my life was, well, awesome compared to being a full time employee.  I worked from home largely, kept plugging away on Pluralsight videos and made good money.  Then I took a subcontracting, travel-heavy gig, and my free agent career began in earnest.

I worked like a dog.  I spent days at a client site, teaching developers TDD and other XP practices.  And then I spent nights advising my former employer and a few other clients, working on my business infrastructure, and continuing to produce content.

And the whole thing was both liberating and terrifying.

I’m an introverted, type A, risk averse person.  This was not a natural career choice for me.  Working as a solo consultant is, above all else, an uncertain endeavor.

It Scares You Into Weird Hours with Uncertainty

To understand how you’ll spend some of your time, consider this random sampling of stuff from my life over the last two years.

  • Some guy said I need something called errors & omissions coverage.  What is that?!  Am I going to get sued?
  • WTF is “self employment tax” and why does Turbo Tax think I owe the IRS $10,000?
  • Do I write a proposal, or should the client?
  • LLC, partnership, S-corp, C-corp?  My head hurts.
  • This big company wants to pay me to consult, but they say I need insurance.  Is that a thing?  What?

These things and many more come up as surely as production defects.  And, like production defects, they force you into hurried action at odd hours.  During the engagement phase, you duck out for hushed phone calls and look into them at nights in hotel rooms.  During operations phase, they burn half a day of your time that you meant to spent on something else.

It Provides Dizzying Highs

Freedom, big paydays, and rushes tend to characterize consulting.  I started out (foolishly) charging $125 per hour for anything I did directly, and even less at times for steady work as a subcontractor, reasoning that I was new and should price low.  This was a mistake.  I was trying to stuff my calendar the way a wage employee would, rather than picking my spots with big paydays.

I would learn and correct this, however.  If you charge $200 per hour, you make $30,000 per wage-month, meaning you can earn a software engineer’s $120K by working 4 months of the year.  I had a lot of great experiences in general:

  • There’s nothing like taking time off between gigs after a big payday.
  • I love the freedom to own my own schedule and shop for groceries on Tuesday morning if I want.
  • I remember feeling like the Monopoly Guy the first time I pulled in $25K for a month, and later thinking that was cute when I pulled in $50K.
  • But I can’t say that I remember the first time my travel status resulted in an upgrade to first class flights, since that happens a lot.  Seeing the world in style while you travel is a blast.
  • Having a client tell you that you saved their program or set them on a much better course is amazingly rewarding.
  • Clients offering you a full time position, ya know, if you’re ever interested, is flattering.
  • And having clients tell you, on check-in calls much later, that you made a huge difference keeps you coming back.

Should I incorporate? The monopoly guy here thinks the answer is yes, and so do I.

Once you start creating valuable outcomes and bringing in good money, the operations “season” can include sanity breaks and nice vacations.  It can also include more long range planning (more on this soon).

It Gut Punches You with Existential Dread and Sadness

All of this probably sounds incredible.  Huge chunks of revenue and rewarding engagements followed by vacation and downtime.  But it’s definitely not always like that.

  • There’s nothing like taking time off after a gig with a payday and then taking a lot more time off because you can’t find work.
  • After that, the freedom of your own schedule seems doubly ironic and cruel when you spend a week putting together a proposal only never to hear back from a prospect.
  • I remember the first time I pulled in less than $2,000 in a month and feeling worried, and then finding that cute when I made less than $2,000 in another month and had also had to unexpectedly pay $7,000 to repair a leaking roof.
  • Spending months holed up alone in a hotel room in the middle of winter quickly becomes lonely.  I mean, Space Oddity times Rocket Man lonely.
  • Software puts people out of work indirectly, and you live with that.  IT management consulting sometimes requires you to put people out of work directly, and if that doesn’t keep you up nights, you aren’t human.
  • Being a constant short-timer and independent means you don’t really develop social relationships and you can’t really count on business relationships.

All of this created in me a tendency to over-correct and dive heavily into long hours.  I did this in all “seasons” feeling like the world was ending if I didn’t have work lined up.  Outside of engagements, I lamented having no revenue, and during them, I lamented not working enough on business.

And, Good or Bad, Solo Consulting is Always Weird

As a wage employee, I’d see organizational weirdness in passing (and often categorize it as a blogger).  As a consultant, people call me in specifically to look at weirdness, and I move through far more companies than an employee does.

  • No matter how many client codebases I look at, there’s always something that some ostensibly clever engineer did in the code that really tests my poker face.
  • I’ve seen scaled agile methodologies with workflow schematics more complex than any of the actual software they build with them.
  • You wouldn’t believe how many people view outside consultants as therapists.  People tell me about how they hate their bosses, how they think their coworkers are secretly drunk, why there are elaborate conspiracies in the office and more.
  • The armies of other consultants places bring in are just as weird.  I’ve seen enough silver bullets that I could gather them all and go be Van Helsing in Romania or something.
  • Enough travel alone produces weird sights.  I’ve been around for people breaking into a hotel pool and a guy getting dragged off a flight for shouting about terrorism, among other things.
  • You realize, top to bottom, how much everyone’s really just kind of winging…. everything.

All of this encapsulates the insane variety of my life over the last number of years.

My Eventual, Gradually Intelligent Plan for It All

This had been my life for years.  But if you think all the way back to the beginning where I described my life as a bearded hermit in the woods, it’s not my life anymore.  So what happened?

In short, I recognized the growing importance of a long game.

A serial consultant helps a client in exchange for a chunk of money, then moves on and does it again.  This is remarkably like the life of a wage employee, but with more boom and bust.  The only long term equity you build in anything is a function of how much you stick in a 401K or IRA.  It’s a career-long commitment.

But I vaguely saw another path.  I had already started earning passive income through Pluralsight royalties, as well as a bit of income from my book and the blog.  I read the Four Hour Work Week and it crystalized in my mind the power of earning money in a way that didn’t directly involve your time.  Then I formed a plan.

Creating content earned me a little passive money.  And creating content helps enormously with the operations “season” for a consultant over the long haul, prompting business to come to you instead of the other way around.

So I burned the candle even more at both ends, making money consulting while simultaneously creating lots and lots of content.  At first, I did it for free, but then more and more tech companies started paying me to do it.  And that money became pretty good — I earned a nice chunk of change raising my own profile.

The Consulting End Game

The fatigue and the boom and bust nature of the serial management consulting life led to a few realizations last year.

  • I was tired and wanted to do lower touch things, working from home (or wherever).
  • I also wanted to decouple my earning from my time more and more.
  • Having a line of business besides consulting really evens out the boom and bust cycle.
  • With a lot of say in my own income, I can improve my life by making more, but also by needing (and making) less.

So I came to a decision.  I would de-emphasize high-touch consulting work in favor of business building, while simultaneously lowering my life footprint.  In accordance with this plan, we downsized our lives, went to stay in the woods, and I got off the consulting carousel to focus on business building.

It’s gone well so far!  I thought we’d need a runway to draw down on savings while getting started with the businesses, but they became revenue-positive for us right off the bat.  Life is good.

And I still do consult from time to time.  I had a nice engagement this summer that involved a couple of weeks of travel.  But I brought my wife with me, we made a trip of it, and I had fun both personally and professionally.  And then I went home to resume my life in the woods.

This is a good life for me.  It’s more predictable, generating steady revenue with less frantic work.  And, when a well suited consulting opportunity comes along, it’s just that — an opportunity, rather than my income life blood.

A Day in the Life Revisited

I’ve learned a lot from this journey.  And, one of the things that I want to do with this site is to help software developers considering the solo consulting journey (which I’d suggest everyone do).  I’d like to help take the lows and uncertainty out of it for all of you by encouraging you to learn from my blunders.  You won’t need to wonder what E&O and self employment tax are.

But that aside, what’s a day in the life of a consultant like?  In some ways, as hard to categorize as “a day in the life of an employee.”  But, aspirationally, it should be easier.

As a solo consultant, you should create a plan for how to spend your time.  That plan should, obviously, include the four seasons and finding clients, delivering value to them, and improving your offering.  But it should also include a strategy and carved out time for your long plays: creating content, giving talks that raise your profile, and developing an offering other than dollars for hours.

And, best of all, you can start with all of the long play stuff while working for someone else.  If you do it strategically, you can have all of that taken care of before you ever strike out on your own.

So after this epic post, what’s a day in the life of a consultant like?  It’s a constant struggle to help people in the moment while keeping your eyes on a longer term prize.

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Aaron Zalewski
6 years ago

Excellent post, thank you! I am particularly interested in why you describe long term engagements as a “siren song”? I have been independent for 6 years. 3 of which was spent at my 3rd client. There I made the mistake of remaining hourly. Currently I maintain an agile R&D posture to my services; hourly to assess and propose for 30-45 days, then fixed bid for 3 month contracts. But this is a repeatable process where the client lines the next one up. My downtime is minimized. I see this as a good arrangement. What pitfalls are there in a long… Read more »

Mark Johnston
Mark Johnston
6 years ago

Erik – fantastic post! Thanks for sharing from your personal experiences. I’ve found myself wondering about some of the details you’ve described here when reading your book or other posts. I think one of the big factors that causes many would-be consultants to struggle is family commitments – specifically children. Before my my two children came along, I was more open to travel as well as the risks involved with the freelance lifestyle. But the pressures of supporting a family make the pragmatist’s role seem far more enviable and tolerable. I’m still looking to move forward with some of your… Read more »

6 years ago

Great post, thanks for sharing! Always like to read personal stories.

These questions are also right on the spot:

– Some guy said I need something called errors & omissions coverage. What is that?! Am I going to get sued?
– WTF is “self employment tax” and why does Turbo Tax think I owe the IRS $10,000?
– Do I write a proposal, or should the client?
– LLC, partnership, S-corp, C-corp?
– This big company wants to pay me to consult, but they say I need insurance. Is that a thing? What?

Maybe you could answer them too?

Denise M Tinsley
Denise M Tinsley
6 years ago

Erik, recently your online content has been aligned around navigating the life of a freelancer. I have a problem I have run into and it has to do with when to say “no” to work. You listed these criteria in this blog entry Is it a short term engagement (a few weeks or less)? Will it pay enough really to be worth it? Can I do it from anywhere? Is it a high value, high leverage engagement for the client? I have the chance to work on a project where my gut says I should not, not only is the… Read more »

Erik Dietrich
6 years ago

I’m filing this away as a good reader question post subject, since firing clients/turning down prospects is both important and delicate. But I do have a quick, overarching piece of advice for saying no — do it by saying yes somehow. In other words, instead of “no, I won’t do it,” it’s “well, I’m not a great fit for you, but would you like the names of some people I think would be better suited?” Basically, it’s a matter of always helping the client no matter what, even if it’s helping them find someone other than you to do the… Read more »