The season finale of Unsure? Insure!

It’s been one whole year of producing weekly Unsure? Insure! episodes. We look back at the most popular episodes, common themes, recurring patterns and the all important takeaways.

It’s been one whole year of producing weekly Unsure? Insure! episodes. The whole reason we started this podcast was because there’s a lack of information out there about how insurance can help freelancers, and also how to manage common risks and tackle problems if they do arise. The goal of Unsure? Insure! was to highlight that there is help available.

At With Jack our mission is to help you be a confident freelancer. Whilst this is the final episode of Unsure? Insure! in its current format, it will continue to exist in different format going forward. We will revisit the series when we have something new to share, but we are no longer publishing a weekly schedule.

I thought it would be fun for the final episode (in its current format) to go through some of the popular episodes and takeaways, and to share my favourite episodes and takeaways.

What’s a freelancer doing that requires insurance?

The most popular episode is episode #2; ‘What’s a freelancer doing that requires insurance?’.

In this episode we talked about the responsibility you have as a freelancer for delivering work on time and providing work that meets client expectations and standards.

Sometimes things happen outside of your control that can lead to projects getting derailed or clients feeling unhappy with the work you’ve delivered or progress you’ve made. Sometimes a mistake in your work can cause problems for your client. This is why you should have insurance.

The big takeaway from this episode and the podcast in general is that when problems do happen, you, the freelancer, are rarely the root cause.

Yes, you can make mistakes in your work and you should have processes in place to reduce the likelihood of problems arising, but the bigger risk is always going to lie with things outside of your control—like your clients.

You don’t have control over their behaviour or expectations. You don’t have control over their reaction to events or what happens internally within the team. This is where a lot of problems start.

When we urge freelancers to consider insurance it isn’t because we’re implying you’re terrible at your job and are accident prone. No, most of our claims come about due to events and circumstances that freelancers have little control over.

By being insured you’re transferring that risk to the insurer so your business can escape as unscathed as possible and you can focus on your biggest asset—your productivity.

Client wants me to finish our project and is asking for damages

The real stories we shared proved to be popular with listeners. The most popular story being episode #7; ‘Client wants me to finish our project and is asking for damages’.

This project had missed various deadlines due to the scope changing throughout. The freelancer’s client asked them to the submit the work they’d done, but then demanded the freelancer pay them damages because the work was overdue.

The stories we’ve shared over the past year seem to follow a similar pattern. Mostly they’re to do with poor project management either on the freelancer’s side or the client’s side—even sometimes on both sides!

If you have good workflow practices in place projects should generally progress without a hitch or fires can be put out pretty quickly.

Consider workflow practices like not starting work without a deposit, having your clients sign a contract, detailing what work is to be expected with a project scope, solid communication throughout, documenting everything, getting client sign-off, setting and sticking to boundaries…

These best practices won’t guarantee everything goes smoothly all of the time but they will reduce the risk of projects or clients going off the rails.

Those were some of the most popular episodes and takeaways for listeners, but here are my top five episodes.

Top five episodes

Episode #48: Having a law firm on retainer

This is the episode we heard from With Jack customer, David, about his experience using the legal advice helpline to help him recover money he was owed from a client through small claims court.

The big takeaway here was how versatile the legal advice helpline is, in this instance helping to guide David through everything from the potential cost of small claims court to filling out the paperwork.

David was able to recover some of what he was owed so there was a positive outcome. The cost of the helpline is included in your legal expense insurance, which costs around £5.50 a month.

Episode #50: A first-hand account of pursuing a payment through small claims court

Many freelancers have considered pursuing clients through small claims court for late payments as a last resort so I wanted to hear first-hand from someone who had done it. Was it worth it? What was involved? How much did it cost? Were they successful?

I’d recommend this episode to anybody who’d like to learn a bit more about the process. Chris was very candid with his experience even though the outcome wasn’t ideal.

If you have legal expenses insurance and are experiencing issues with non-paying clients the debt recovery service might be able to help you.

Episode #46: Be a confident freelancer

I recorded this episode during a period of frustration. We had a string of freelancers contact us who were experiencing similar problems with clients trying to take advantage of them. In many of these situations the freelancer didn’t have the confidence to stand up to their client even though they knew they didn’t deserve to be treated that way.

This episode was intended to get you feeling confident to stand up for yourself if a client is treating you unfairly.

Some freelancers struggle with setting and sticking to boundaries because they don’t want to deal with conflict and feel uncomfortable telling a client “No”. Or there’s a fear of losing a client so freelancers overstretch themselves to accommodate clients.

Being insured should give you the confidence to stand your ground with clients who try to mistreat you or extract more value from you than has been agreed. If they do ever take things that little bit further your insurance is ready to step in and help.

Episode #37: Keeping projects on time and managing client expectations

I spoke to several well-established freelancers for this episode about the processes they have in place to ensure that projects run on time and to make sure their clients are on the same page as them for the duration of the project.

A lot of the claims we see stem from poor project management (not always because of the freelancer) and in this episode we focus on processes you can implement to ensure that your workflow is solid and your project management is on point.

Episode #16: Professional indemnity insurance teardown

Most of the episodes that listeners enjoy are story-based, but this episode is worth a listen for anybody who doesn’t fully understand their professional indemnity insurance because this complex product is broken down in a way freelancers can relate to.

It’s a very meaty insurance product. Because there are so many moving parts to it a lot of the valuable features can be hidden. In this episode I go through the policy features and talk about how they apply to you and the work you do as a freelancer.

The big takeaways

After one year of producing weekly Unsure? Insure! episodes I started to sound like a broken record. Similar patterns cropped up and there was a recurring theme across each of the episode’s takeaways.

  1. You have to approach every single project—whether it’s a new client, an existing client or a friend—with solid processes in place. Processes that will help you meet deadlines, processes that will ensure you and your client are on the same page at all stages of the project, processes that will help you manage common problems like the scope changing throughout the project.
  2. You must approach each project with confidence. Confidence in your skillset, confidence in your pricing, confidence in your workflow. If you aren’t confident some clients will take advantage of that. You’ll end up doing more work than what was agreed, or working on projects you’re no longer enjoying. It’s a slippery slope.
  3. You absolutely should consider insurance if you’re providing any kind of professional service to clients. Most problems stem from the unpredictable nature of clients or things happening outside of your control. The one bet that you can put on is that lifeline insurance gives you if things do go wrong. Most freelancers will never have to use the practical side of their insurance (which is the legal assistance), but every freelancer will benefit from being insured on an aspirational level because it helps you be a confident freelancer. It helps you go into projects confidently, it helps you handle clients confidently and it helps you confront problems condidently.

Having solid processes in place, approaching each project confidently and having insurance will help set you up for a solid freelance career.

We asked ourselves one important question…

What do we want out of an insurance provider?

With Jack is the answer