Four freelance lessons learned the hard way

An interesting thing about working as a freelancer, while the area of expertise may vary, is that many of us will share the same experiences time and again.

Even without a connection in the fields in which we freelance, there are some lessons that are universally relevant, and that certain experiences will come to teach us.

When working in any field the last thing you should ever expect is to reach a point where you have nothing left to learn. So we tend to approach each experience with knowledge hungry arms wide open. Looking to learn whatever this new project or interaction will teach us. Only sometimes, the things we learn are not always pleasant. Or easy to take.

In fact, in a turn which makes their impact even more depressing, most of those unpleasant lessons we seem to have to be learnt the hard way.

In the interest of paying it forward, and perhaps helping others learn these lessons from our freelance trials and tribulations without having to suffer through them on their own; we have put together some helpful advice.

Contracts are not guarantees

You see the advice given all the time, hell we’ve even promoted this pearl ourselves in a post or two. Everyone tells you that you should never work without a contract. It is just good business.

However, the part that is not shared as often goes a little bit something like this: contracts are not guarantees that things will go as agreed, or that you will even get paid.

You see without proper funds to pursue broken contracts in court, a contract is little more than a threat.

Sign image via Shutterstock

And for us working here in Colorado, we have other challenges that are more than likely not unique to our area. Given a recent judges ruling in Colorado that contracts with anyone operating a business in the MMJ industry are meaningless, taking clients to court over contract failures is not always a worthwhile effort that is guaranteed to pay off or come down in our favor.

What to do?

Does this mean we should just throw caution to the wind and work without some sort of signed agreement in place? Of course not.

Though it may not be a magic recipe for success, it can prove to be a powerful and useful deterrent. A good way to knock some potential problem clients out of consideration. If they aren’t willing to sign, then more than likely you do not want to work with them anyway.

What works in our favor here is that clients do not know where we stand, and do not know whether or not we would be able to pursue the broken contract in court. Sounds like we’re gambling either way we work it, but that is not entirely true. In fact, some would say, and we would agree, that the risks are much higher working without a contract in place to offer you what protection it can.

Consider what Dante said in Clerks, “…theoretically? People see money on the counter and no one around, they think they’re being watched.”

Honesty through paranoia is one of the ways that contracts can act in our favor. As long as there is a perceived actionable threat, many potential clients will adhere to the contract. So it can be a motivator for things to stay on track with the right clients.

Red flags should never be ignored

Some of us, yours truly included, like to try and see the best in people. And as such, we tend to not want to rush to judgement and start forming our opinions too quickly. This is at odds, however, with working as a freelancer. Making it a habit that we have to compromise.

Our prosperity in the market is based on being able to judge clients and projects quickly and decide if we are the right fit.

So when we start seeing those proverbial red flags popping up in our initial meetings with potential clients, one half of us may be calling for us to ignore them and wait until we have more information to form our opinions; while the other screams for us to cut and run.

Often times we will ignore the voice of reason, and we will ‘take a chance and take the job’ or linger a little longer than we possibly should before bowing out. Potentially missing out on other opportunities while we hold on too long.

What to do?

Most of the time people will say that one thing you should never do is to get personal. However, in this case, it really is the only thing to do.

We need to set our own personal limits and boundaries for the sake of our business and emotional well being. Not only must we determine our own limits, we have to understand how much each of these flags means to us. What one person sees as a game-ender, others may consider a mere game-changer. One they can work with.

Stop image via Shutterstock

So we have to establish boundaries and prioritize these flags in a very personal way in order to safeguard against less than favorable project outcomes. This does call for a fair amount of self-awareness and objectivity. Both will play heavily into determining how many, and which red flags we will bare and which ones we won’t.

If we are not self-aware enough, then we may not judge what we can put up with correctly. If we are not objective enough, then we risk compromising our professionalism and crossing into what may be perceived as pettiness as we let things get perhaps too personal. It truly is about finding that balance, and drawing our lines firmly in the sand.

The client’s wrong, doesn’t mean you’re right

One pitfall that is easy to fall into comes with the assumption that if the client is wrong about something, that automatically puts us in the right.

This is a lesson that can cost you a project or two before you fully realize what is happening. With calls going out all across the internet that sometimes the customer isn’t always right, we have to understand that our expertise doesn’t always guarantee that we are.

In fact, many will speak to being somewhat humble and never forceful when we feel the client is pushing the project in a bad direction. But if you are of the mind that our expertise is what we were hired to provide, and we do not push for it to prevail in some instances it can be harmful to the success of the project.

Crash image via Shutterstock

Whenever a disagreement arises between the two visions, and the client’s is easily seen as ineffective, that does not mean that we should just move forward with our own. Or demand they reconsider.

What to do?

Once again, this comes down to a very personal decision. Do you want to remain on a project that is doomed to failure just to get a paycheck which may or may not be waiting? Especially if the project’s been rendered ineffective by decisions the client forced us to adapt to, and they see this failure as being our fault.

Is it going to be worth, what may be a fight, to get your money?

Not to mention the potential effect of having your name attached to a bad project could have on your reputation. It is more than likely not going to help secure you any future work if the project tanks. So we have to decide which decisions we cannot stand by while implemented.

We have to gauge with each project if there is a point where we feel the success rate has been compromised too much for us to see it through.

At that point, we owe it to ourselves to bow out and let the project go, rather than deliver a project whose failure could be levied against us. If the client wishes to push the blame our way, and take action, then we may have painted ourselves into a corner we’ve no way out of.

All your eggs in one basket is ill-advised

No matter how promising the offer, or tempting it may be to throw yourself in so completely, putting all of your eggs in one basket, as the saying goes, is ill-advised.

Allowing for a single project to dominate your time until you become content with it being your only focus can leave you in something of a lurch when that project suddenly ends. Even if you know it is coming, when it finally arrives it can present you with some problems.

This is not something that we often intend to let happen, but the truth of the matter is that it does. It is easy to get wrapped up in a project and over-commit or over-dedicate ourselves to the point where no other work gets done.

Blank image via Shutterstock

When freelancing, job security and steady work are not always easy to come by. So when it arrives on our doorstep, many have a hard time turning it away. Which is not always the thing to do.

What to do?

Balance, balance, balance.

Like the Realtor’s chant of location, location, location; freelancers have (or rather, should have) a mantra of balance.

It is key if we wish to keep our schedules from being overrun and ourselves from becoming over-committed. The same goes for when we feel that tendency to put all of our eggs in one basket coming on, we need to push back and fight to find the balance we need to keep other avenues open.

There are numerous ways that we can do this, but it once again boils down to us, and finding what ways work best on a personal level. If strict scheduling and rigid list-making works best for you, then by all means go for it. Divide up your work day or week in shifts or make daily to-do lists to keep you balanced out, and stick to them.

If you come to a point where you find you are unable to keep things in balance, then it may become necessary to reevaluate your commitments and readjust your schedule to ensure that you are not falling into this trap.

To conclude

All of those lessons were learned the hard way by me and countless others in the freelance field. Hopefully, with more freelancers sharing their experiences fewer lancers will have to suffer through these situations to learn from them.

What lessons have you learned the hard way while freelancing? What tips can you share for avoiding them in the future? Let us know in the comments!

Rob Bowen

Rob Bowen is an emerging filmmaker, celebrated author/podcaster and poet, and most recently the co-founder and imaginative co-contributor of the creative design and blogging duo at the Arbenting and Dead Wings Designs.