What traditional work can learn from the freelance economy

It must be tough being a freelancer. No company holiday party. No vacation. No benefits. Who in their right mind would choose this?

If this is your thought on freelance, your pretty spot on, and definitely not alone. Freelancing is tough. It’s not a “4 hour work week” spent blogging on a beach.

But you know what can be worse? Having a job. Which is why around 70% choose to freelance according to the McKinsey Global Institute, 47% of millennial’s currently freelance, and 74% of millennial’s say they’re interested.

As someone that’s done a full circuit around the freelance sun (freelancing, leading freelancers, building freelance platforms, and selling out as an FTE), I can promise you it’s NOT a cage match of freelance vs. full time employment. Both have pro’s. Both have con’s.

And for both sides, there’s things they can learn from each other. For example, while freelance can learn from full time employment’s career progression, full time employment can learn from freelances flexibility, personalization, and outcome based environment (no politics).

In this article, I hope to illuminate learnings from both sides of the fence 🙂

What can full time employment learn from Freelance? Let’s find out!

Let’s Level Set, I’m a Full Time Employee, and Freelance Doesn’t Always = “Gig”

I always like to make sure you as a reader have the all the ammo to call BS.

Your first piece of ammo, is that I am a somewhat happy full time employee. I love the work I do, specifically the opportunity to help organizations embrace freelance at scale, and the people I get to do this with. I have a salary. I have a boss. One hell of a boss. And if I need a sick day, I still get paid.

Your second piece of ammo, is that I am being very picky, like that friend who only eats a PB&J without the crust.

Throughout this article, freelance = highly skilled knowledge work (no different than what you’re probably supposed to be doing right now instead of reading this).

As an industry, we’ve done a great job of confusing people with various terms.

When I told my parents I freelanced, they thought this:

When I told my friends, they thought this:

In reality, when we cut through all those buzzwords (freelance, gig, crowdsourcing, human cloud, elastic workforce, etc.) I was this:

Yet instead of baggy khakis and New Balances, to customers/clients, I looked like this:

InnoGeek Group, my strategy consulting firm clients engaged with

*InnoGeek Group – the strategy consulting firm my clients engaged with.

I usually started with market research, then dove deeper with my clients into business planning, financial modeling, honestly anything I could teach myself through Youtube.

The difference between freelance and FTE me is that I wasn’t in the office, I was at a coffee shop (this is merging as we speak). I wasn’t working for a company, I was working for a project. And rather than submitting resumes, I connected straight to whoever needed me (industry term is direct-to-talent, or direct-sourcing). For myself and other freelancers, this commonly is facilitated through freelance platforms like Upwork, Business Talent Group, Catalant, Gigster, to name a few.

Freelance = highly skilled knowledge work

Lessons From My Freelancer Lens

Now that you can grill me on being a corporate sell out and being too picky, let’s dive deep into some things that just don’t make sense to a freelancer in full time employment 😛

1: Not having one bad boss

Did you know that 58 percent of people say they trust strangers more than their own boss?

And that 75% of people leave because of their boss?

Based off these numbers, why does full time employment generally mean one boss?

When picking a spouse…I get it. But when the only thing lower than the divorce rate is employee engagement (around 30%), and the driver to that is a horrible boss, seriously what the hell are we doing?

As a freelancer, we had a couple of controls against this.

First, there is no one boss.

Second, there is a trial period. Clients expectations are unrealistic? Client is a micromanager? Guess who’s not extending the contract?

Third, freelancers have the power of crowdsourced ratings and reviews. Professor’s are already well aware of this dynamic through Rate My Professor.

As I learned when finding my own ratings page, we truly are transitioning from employees beware, to managers beware.

For context: Clients: 6 Things to Avoid if You Want to Attract the Best Freelancers

Multiple clients, a trial period, and crowdsourced ratings review protect Freelancers from one bad boss

2: Autonomy of WHAT to work on

I’ll admit it, I’m pretty bad at doing anything I don’t want to. Maybe it’s an only child thing, or an entitled millennial thing, but tell me what to work on instead of enabling me to choose, and I’ll probably put the effort in below.

20 years ago I’d have to “grow up” and be happy with what’s given to me. But today, everything from what we eat, how we get around, to even how we date, is personalized to exactly what we want and when we want it. Which is probably why we keep hearing stats about millennials not staying long enough at one company.

How can we settle for working on something we didn’t choose, when abundance of choice is our default? Whether how we get around, how we eat, even the choice of who we date is personalized on a silver platter.

Why would work be different?

In freelance, it’s not. Projects are available at the push of a button. And the more freelancers build up their digital trust, the more room they have to reject and/or take on projects not directly in their skill/industry swimlane.

*In my experience, freelancers have 2-5 awesome clients they stick with.

As a freelancer, it’s not like you can choose any project you want right away. If you don’t know how to code, yet you want to build a mobile application, you’re in for a rude awakening. But say you do know how to code, and you’re interested in the medical industry, the entry point for dipping your toes in medical is significantly lower. Maybe you help build a medical mobile application? Or instead of years trying to break into the field, maybe you spend a week helping build their scope document?

Here’s a screenshot from Upwork when I searched “freelance medical mobile application project”.

Yes, you may have to take lower pay initially to build up credibility. But doesn’t a couple weeks sound simpler than freeing up headcount? Or in the case of the second project, less than 1 month, at less than 10 hours a week.

The important takeaway for full time employment, is that freelance is worker directed, meaning the freelancer has the choice to work on what they want.

Freelance puts the power of WHAT to work on in the hands of the freelancer

3: Real time, transparent feedback

It seems that in corporate America, you can’t open your left eye without seeing a plug for having a “growth mindset”. Simply put – a growth mindset means when you trip in front of people, you laugh it off, learn from it, and never do it again. Or in my middle school case, you present a book report with your fly down, get laughed at by the class, feel super embarrassed, but use it as a teaching point to check your fly every time before going on stage.

In both cases, practicing a growth mindset can only happen if you receive real time, on the spot, and tangible feedback.

So if you’re annual review is 7/1, you present with your fly down on 7/3, and you don’t learn about your mistake until the next year, will you really learn from it? Or in a more “real” manner, if you’re boss says “you’re doing great”, do you know actually know what was so “great”?

Like all these points, the growth mindset isn’t exclusive to freelance. But freelance feedback is real-time and tangible, inherently promoting the growth mindset.

Real-time, meaning once the milestone was completed (every two weeks), feedback was given.

Tangible, meaning it is demonstrated both quantitatively (ratings) and qualitatively (reviews). It also is hyper focused to tangible variables (speed, quality, cost) outlined in the SOW, while leaving room for more general variables like communication, professionalism, etc. So instead of “you’re doing great”, the client can say, “you didn’t deliver on time, you didn’t properly communicate what you needed up front, this element isn’t comparable to the element we agreed upon, you didn’t communicate the deliverables in a concise manner, etc.”

Freelance enables the growth mindset by providing real-time and tangible feedback

4: Controls to optimize Flow

Intuitively it makes sense, the more your employees aren’t in the office, the more they’ll “slack off”.

But in practice that’s not true. Instead, as a 2 year Stanford study would show, employees become more productive.

I won’t speak on behalf of Stanford, but for myself, my productivity in the office vs. out of the office is night and day. Whether on a plane, in a WeWork or a hostel in Singapore, when I have control over my time (no drive by office distractions) I can proactively optimize my time for the output needed.

The reason for me, is that not all work is equal. For some tasks, I need to be a cognitive warrior, which requires being in flow states that result from a specific environment – good music, and zero distractions for multiple hours. For other tasks, like answering most emails, most data input tasks, I just need hours, and can handle being interrupted every three seconds.

When virtual, I can proactively schedule work in accordance with these requirements. If flow is needed, I can turn off my phone off, silence all notifications, and work when I have my best energy – for me, some reason it’s 9-2 (pm to am). If I just need hours, it doesn’t matter where or when it is. And if I need collaboration, there’s plenty of digital tips/tricks to foster equal, if not better collaboration.

Once again, the above is NOT exclusive to freelancing. BUT – whether it’s the implicit assumption you should be in the office 9-5, or an explicit understanding, the virtual, project based environment of freelance enabled me to proactively control my time in favor of flow.

Sidenote – whose idea was it to go fully open office spaces? In my first experience as an FTE, I was all jazzed up for the open office concept. Then a month in, I was so burnt out and became a hermit, finding any and every spot to avoid humans. Turns out I wasn’t the crazy one, as the first page of Google agrees just open offices are a bad idea.

By unlocking where and when you have to work, freelance puts the power of Flow in the hands of the freelancer

5: Controls to mitigate the bad boss

Let’s talk damage control. What happens if you get the bad boss?

Do you quit? Possibly…

But in order to not perpetuate the millennial stereotype of us quitting when the road gets tough – how might we perform under bad leadership?

Let’s look at four common failed leadership scenarios:

A: Priorities/tasks changing with the weather
B: Scope creep
C: Unclear expectations
D: Multiple people working on same thing

A: Mitigating a boss that changes with the weather.

On Monday your supposed to do one thing, on Tuesday a whole different thing, then on Friday you were really only supposed to do that thing on Monday.

Freelance can mitigate this by proactively protecting from this in the terms, along with leveraging collaborative technology tools like Microsoft Teams, Slack, Trello, and Jira to name a few, to make this actionable.

To proactively protect team members and myself from this situation, my MSA had two clauses:

48 hour rule – No freelancer is expected to answer an email within 48 hours. Once a month, the client can pull a P0 and expect an answer within an hour. *If it’s a freelancer mistake that needs urgent attention – it doesn’t count as a P0.
Pay per sprint – The Freelancer is only expected to deliver agreed upon deliverables per sprint period. Generally, my engagements ran by two week sprints. On Monday, we’d outline each required task, and the next Friday we’d review each deliverable. If a task wasn’t agreed upon Monday, it wasn’t expected to be delivered. So when the leader emailed you saying “do this email campaign” on Tuesday, that email would be on hold until the next sprint period.

As Mike Tyson would say, “everybody has a plan until they get punched in the face”.

To weather the various punches, freelance can use the digital first tools it already inherently uses to handle communication, collaboration like file sharing and real time editing, and task management.

For example, Microsoft Planner, Trello, or Jira are a few tools used specifically for task management. When you do get that zinger email, “I need this now”, instead of dropping the world, you can point them to your planner board, and ask which ticket(s) should be dropped.

Along with maintaining transparency of the team knowing why you had to change course, this protects your accountability, as you no longer are expected to deliver the deprioritized tickets.

Freelance keeps a bosses changing priorities at bay combining collaborative technology tools with clear prioritization protecting terms

B: Mitigating a bosses scope creep, or the “ever changing goal post”.

Have you ever been told: “Hit this crazy deadline by 5/1, then when you do, I’ll act like it was expected, and make an even more aggressive 6/1 number. Don’t f** it up!”

Or even better: “Aww you hit your goal early. It must not have been big enough. Here’s your new number, better get started immediately!”

It’s not the horrible bosses fault (per se). Rather a misalignment of incentives. Since employees are on salary, why would a boss tell you, “you did good, now take a month vacation to Tahiti”.

In contrast, freelance is outcome based, and the SOW aligns incentives with cost & quality rather than keeping you busy.

Let’s take my favorite project, one that led to a surf trip. The cIient was a strategy consulting firm, and they needed to evaluate whether or not to launch a customer experience offering (I know…consulting for a consulting company). We scoped a 4 week engagement, and broke it into two, two-week sprints. Sprint one was researching if they had an in-house strategic advantage. Sprint two, if there was a strategic advantage, was to create the business plan. Admittedly, I didn’t add a continuity clause, so if I advised against pursuing, they only had to pay for sprint 1.

After sprint 1, which was delivered on time and on budget, my advice was to not pursue. Rather than keep me busy, we ended there, BUT, the best part, is that the champion director was extremely appreciative, and told me, “great work, we’ll pay the next sprint, go do something fun”.

If you’re thinking why the hell would he pay for the extra sprint, I thought the same thing. Then I realized as an FTE, I would have budgeted for the full project anyways, and whether two weeks or four weeks, the outcome was consistent – whether or not I should pitch leadership to go forward or not.

“Freelance replaces a salary for a scoped outcome, replacing your bosses incentives for ever-increasing goal posts”

C: Mitigating a bosses unclear expectations, or “just make magic”

Whether Moses parting the Red Sea, Napoleon on his horse, or your boss, the assumption is that they got to where they are because they know/understand the details of what they’re telling you (or the sea) to do.

In reality, following most bosses looks more like this:

I don’t think it’s a management requirement to lack an understanding of what’s required, or “delegate without the details”, but too often employees AND clients are expected to be a mind reader.

The difference, is that freelance has controls against this.

As we learned about above, the “rate my professor” functionality will help you avoid bosses as such. But if you’re brave enough to take on the challenge, the pre-work, or scoping, should outline comparables in order to align expectations.

As a freelancer and engaging freelancers, my SOW has a clear clause for three comparables.

But it doesn’t have to be just the SOW.

For organizations, wherever you lead all your employees to, it could be an intranet site, a wiki, you name it, but you can show case studies of past projects, so employees know what to expect, and possibly you can even provide the SOW or project descriptions so they can replicate.

Communicating, displaying, and agreeing on comparables replaces magic with aligned expectations

D: Mitigating multiple people working on the same thing

Isn’t it great when you skip your kid’s birthday to finish a deck, only to realize Larry down the hall built the same deck a week ago.

To avoid this, you could have just done that crazy thing called talking to each other. Or tracked everyone’s tasks through a spreadsheet. But let’s face it, how often does that last until the next watercooler conversation, or that “next big idea” your boss has?

Remember those collaborative technology tools discussed in maintaining prioritization? They are GREAT at avoiding against duplication of work.

As we see below, if you’re leveraging a scrum board, and making sure the actual tickets have the assigned members and relevant files, duplication is pretty controlled against.

Once again, this is not unique to freelance!!!! In the picture below, in order to bridge the old with the new, I made a physical scrum board on the wall outside my office.

The difference is that since freelance is virtual, project based work, there is little to no room to NOT be transparent.

6: No HIPPO’s

If you’ve made it all the way to here, you probably sense my frustration with most leadership.

You know what my biggest beef with full time employment is? Those damn HIPPO’s!

Remember that organizational behavior class where the professor mentioned the HIPPO’s (highest paid people in the office), and you laughed, thinking “that’s ridiculous, decisions are obviously driven by data & merit, not any one person’s ‘opinion’”.

Then you sit in your first meeting, and watch the room become docile when the person at the head of the table weighs in. Frank in the corner says “what a great idea!!!”. Then after the meeting, the same Frank says, “what the f*** are they thinking.”

It’s not Franks fault per se…his bonus heavily weights on the HIPPO’s opinion. As does everyone in the room.

But what happens when you don’t have “one boss”, or in a freelancers case, no boss at all?

According to Elaine Pofeldt, from her work studying hundreds of entrepreneurs tapping into freelance for her book The Million Dollar One Person Business:

“Some entrepreneurs find that relying on these outside providers creates a more positive, egalitarian relationship than many managers have with their staff. These entrepreneurs see the people who support them as trusted partners, not direct reports whom they have to supervise. They are all part of a community of individuals who are building business simultaneously and symbiotically.”

Supporting Elaine’s findings (and discussed in The Power of Freelance Teams), my freelance teams are results driven and truly horizontal. Admittedly, from a thousand feet above, they probably look more like a bunch of middle schoolers playing XBOX in their own living room than a bunch of professionals doing “professional” things.

*Technically, you could consider the client a HIPPO. BUT – just like we discussed in having one boss, if the client sucks, instead of “managing up”, you can “manage out”, meaning not working with them. And instead of a boss deciding your annual bonus, reward is driven by your execution of the SOW. Were you on time? Did you exceed the agreed upon comparables? The boss is your SOW.

Summary

I started by promising you this wouldn’t turn into Jerry Springer. Hopefully I kept my promise!

Whether full time employment OR freelance, there’s goods & bads. For me personally, the model of freelance is GREAT at mitigating poor leadership (bad bosses/HIPPO’s), maintaining autonomy of what you work on, when you want to, where you want to, and enabling the growth mindset. BUT, this same model in current state falls short in career development.

Here’s my challenge: whether full time employment or freelance, how might we take the good and chuck the bad?