We all make mistakes. It’s what makes us all humans. Making a mistake isn’t the end of the world by any means. However evaluating the mistake and making sure it doesn’t happen again is the key to a successful freelance business.

I’ve made plenty of mistakes in my career. I’ll be honest, it sucks each and every time. I get annoyed, upset, and even sometimes so overwhelmed by it I get silly. After taking a deep breath or even sleeping on it for a night, I’m able to evaluate what went wrong and try to make sure that it doesn’t happen again.

Freelancers tend to think that it’s all roses when they jump in full time. We have a skill that’s in demand. But what we don’t realize at first is we are taking on all aspects of a business, not just the skill that is in demand.

What I want to do is share with you the ones that I made so that hopefully you can avoid making them. I've even posted these on my wall (with the way to not make them again) so that during the day or on a call I can be sure to not repeat them. Don't believe me?


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Positioning within the market

Knowing who your ideal client is critical to your business. I talk about this all the time so I don’t want to do that here.

However I will say that I still make this mistake sometimes. I have gotten pretty good at knowing who my ideal client is, but there are times when I think they are only to find out later than I missed something along the way.

It happens and it’s ok. When I do figure it out, I have a conversation with that client explaining as to what I’m thinking.

This is not just about who your client is, but about knowing yourself as well. Being yourself and working with clients you enjoy and project that you find interesting help you become the expert in your market.

You need to be comfortable with how you present yourself and business. Remember business ultimately is about the relationships between people. If a client and you don’t click on the personality front, it doesn’t really bode well for that lasting business relationship.

For me, I’m a pretty straightforward, candid, NYer. So sarcasm is my second language. I speak frankly to my clients because I care about their business goals. If something is amiss or I don’t agree with a certain idea they have, I want to be able to be open with them about it.

In the past I’ve had clients that didn’t respect that of me. They just wanted me to code what they wanted without any feedback. Of course in the beginning I did it, however it made me unhappy and unmotivated.

Now that’s something that I speak about upfront before they are a client of mine. I want to make sure that they understand what I bring to the table. If they are looking for someone to be 10 fingers on a keyboard, there are less expensive options out there than me.

However if you want 10+ years of e-commerce experience, understanding the psychology of the web, understanding of web development best practices, etc to make sure that your goals are accomplished that’s what I can bring to the discussion.

What I also bring is some reporting, consistent communication through various ways and other things that you don’t get from most developers out there.

Knowing your ideal client allows you to be yourself and enjoy what you do, allows you to figure out exactly what the client sees as value. When you do that, you stand out.

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Taking on a partner

It’s usually a good idea to do what you do best and find someone else to fill the roles to do the rest. So it only seems to make sense to find a partner to work with, right? That’s what I thought.

I found a partner in my first go around in my freelance career. Inside a year I found myself looking at career job boards for my next full time position.

A developer partnering with a designer. A writer partnering with a marketing consultant. A sales person partners with the engineer. These seem to be matches made in heaven.

However this could be end in you having to going back to working for someone else before you get off the ground. Not everyone is a perfect match. Being a partner adds a layer of business that most are not familiar with.

Besides the whole legal aspect, which I won’t dive into, it’s more about personality. You have your own goals and your would-be partner has their own goals. Even though they may be very close, each one of you has their own personal aspects in mind.

You both could be starting a freelance business because you want flexibility in your schedules to spend time with your families.

Partnering could be a crucial mistake if your schedules don’t exactly align. When will those meetings take place?

Since you both have an entrepreneurial spirit, one of you could be thinking about writing a book where the other is thinking about building products. These ventures would cause a rift in your dedication to the service business you are both trying to build.

Pivoting the business is difficult because one person may not see the value in adjusting because they don’t have the skills or personality to shift.

Finding a partner can be a good idea to have someone compliment those skills that you possess. But until you really get into your freelance career, you may need to stand on your own before you find that partner.

Jumping in to every client request right away

We always want to make every client happy. It’s almost an instinct to react and jump at every single client request that comes in. For the longest time I would hear the email notification that there’s new mail and stop doing what I was to go ahead and read it.

Then take some time to think about the response, craft it, and hit send. Then I would go on to read the next email and it requires a “quick change” to some code on another client’s website.

Before I knew it, it was 90 minutes later and I have totally gotten off track with what I was working on in the first place.

This is a mistake all freelancers make. Especially in the beginning stages of our career. (I still do it - shhhh don’t tell anyone).

You don’t want to use your inbox as your to do list for this reason. By doing that you essentially tie yourself to email and being reactionary instead of proactive. You want to be able to schedule and plan out the work that needs to be done in the proper way.

As clients begin to see that you respond to every request within 15 minutes then they get used to that response time. In the beginning you may be able to keep that up. But as you get more clients, this is impossible.

Clients don’t expect you to answer them immediately. It’s just not realistic. Having a window of one business day is acceptable for responding to any emails. It’s even best to tell clients when they become a client what to expect.

Plan out your day and stick to that plan. Make sure that when you plan out your tasks for each day. Don’t add new tasks to today’s list. Making this mistake will throw off your schedule for the entire week, maybe even the project altogether.

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What I suggest and this was a HUGE difference maker in my business to know that I get things done was to create office hours.

Clients know that we have a regularly scheduled call each week. They don’t pick up the phone before that unless it’s an extreme circumstance. They wait until we have our chat on Friday.

I also don’t do any calls on Mondays. This is so that I know I can start the week off strong and without distraction.

Not having these boundaries and set expectations for your clients could be mistakes that affect your ability to grow. Putting these in place early on will not only put you in the habit, but it’ll also make you more professional in the eyes of your clients.

It also shows your clients that you respect them in a way that most freelancers don’t. Rather than the client having to chase down the freelancer. You are telling them “I’m setting aside this time for you each and every week to talk about our project and priorities. This time is only for you and no one else.”

Reacting right away to a potential lead

Getting leads into your freelance business is an absolute must. Without them there is no business. We treat an incoming lead like it’s the last slice of bread on a deserted island. Or that it’s the most precious thing to ever enter into our lives. In fact, before I set up my sales process when I would see a new lead come in, I would stop everything I was doing to see what project they had for me to work on.


This mistake puts any freelancer on our heels. We fear that if we don’t address this lead right this second, they’ll find someone else to do their project.

I’m not saying to ignore it for a week. But what I am saying is remember that project you just put aside? The one that has paid you a deposit already? The one that you have landed and actually will be getting more money from once the project is completed? Yeah that project. That’s most important right now.

The new lead can wait until the end of the day for a response. It’s perfectly acceptable and quite frankly, if you do respond within seconds of them reaching out, you don’t look busy.

Not looking busy positions you as someone who’s not in demand. Someone not in demand doesn’t make the lead feel that they are getting the best. This positioning is a mind game, sure. But it’s also about business. Businesses want to work with the best. Being not busy makes businesses desperate and no one likes desperate.

The other side of this is chances are good that the new lead isn’t a perfect and ideal client. The biggest mistake freelancers make in the beginning of their careers is saying “yes” more than “no.”

If you want your freelance career to be sustainable long term, learn to say “no”.

If you don’t believe me, take a look around the web and all these fine folks who say no often. When you say “yes” you are saying “no” to something else. Something else that is better for your business or existing clients.

I’ve learned to default to saying “Thank you, let me think about it.” So that I can evaluate it against everything I’m doing within my business to make sure that it’s a fit in the long run.

Learn to say “no”. When you do say “no” present some options if there are some. Refer someone else to do the work. Or pass along a link that leads to solving a problem.

Saying “yes” to everything is one of the biggest mistakes freelancers make. Contrary to what Nike says, don’t do it!

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Client work always winning over own

Client work pays the bills and keeps the lights on. There are times though when we need to make sure that our swords are sharpened and our tools are cleaned up and put back in the toolbox.

Not making enough time to work on our own website, business processes, even attending events are critical mistakes that will flatline our freelance business. For the longest time I had a website with services that I didn’t even offer anymore. I think it was a full year before I did anything about it.

For me learning about the newest shiny tech tools wasn’t too hard. What I had a tough time was wrapping my head around documenting processes within my business. However seeing how important it is for the growth of my business, I know have a stable of documents on Google Drive that explains all the repeatable processes within my business from setting up a new client, configuring backups, and even how to post on social media.

  1. We need to always stay on point with our skills, make sure you are taking the time to learn and educate yourself on new things in your space.

  2. Set aside a working capital budget for your business to make sure that you can pay for the conferences and educational course materials. This is investing in your business and should always be on your mind when you want to move the needle.

  3. Attend conferences and events to see what new ideas people are talking about.

  4. Review the business each quarter to see what sort of things you can optimize within the business to increase profits.

These are all things that fall into the category of working on the business rather than in it. This allows freelancers to grow and become sustainable during the rough times.

At the bare minimum, you should be taking 2 or 3 days a month to work on your business. I personally like the 80/20 rule. What I do is basically take an entire day each week to work on my business. It’s scheduled into my every week so that I know that projects are still meeting deadlines, but I’m moving the needle of my business forward.


This could possibly be the biggest mistake a freelancer makes most often. Discounting.

During the sales process there will come a point at which negotiation happens. I’m fallen victim to the illusion that this is all about money. Especially when I knew I needed work, I often times would lower my rate to land the gig.


One thing I want to mention here is that negotiation doesn’t just mean how much the project costs. Everything is up for negotiation.

Know your worth. Know how much you need to make to build your sustainable freelance business per project. Don’t waiver on that. If budget becomes an issue during the negotiation, make the scope of work the focus of the negotiation.

Budget is always what the client wants to maintain most. If it means that the scope needs to be adjusted to fall in line with the budget, then explain why that is to the client.

Often clients think that the scope they come to the table with is the be all, end all for the project. However phasing the project out and only working on what’s most important first can reduce the scope of work as well as the fit inline with the budget. Then the trust and relationship builds during the course of the project. The client sees that you know what you are doing because you’ve delivered on what you promised. Maybe even over delivered too.

This is at which point the client will want to continue to work with you and be able to continue to the next phases of project. Focusing more on the scope and less on the money. Which in the end is a win-win for both. The client gets the full scope, maybe more from their project. You, as the freelancer, get the full payment of the project, maybe more.

Scheduling projects

Just because you are working wherever and whenever you want without someone from the corner office coming over and asking you updates every hour, doesn’t mean that deadlines don’t exist.

Scheduling is critical to any business. If you say you’ll have something by a certain date, you need to have it.

Clients tend to have marketing campaigns or other things that depend on the work that you are doing for them. If you miss, they may miss and lose money. That’s obviously bad all the way around.

If you miss deadlines, those projects that you are scheduling up after the current one also get delayed. Oh, you are scheduling up projects right?

You should be scheduling up projects at a bare minimum of at least 3 months out from today. In fact if you can do 6 months, I’d suggest doing that.

Having this queue of work is needed to avoid the famine of the cycle. If you know you have a deposit to get someone one your calendar for work in a couple of months, that allows you have income now for work later.

This is projection income and having this revenue on a consistent basis means that you won’t have the famine so many freelancers fall into.

Bottomline here is scheduling is important, for you and the client. Don’t make the mistake and miss out on scheduling and just live in the present.

Following up

I spoke about regularly scheduling calls with existing clients each week a bit earlier, however following up is different.

Following up means just taking the time to reach out and see how someone is doing, maybe even to just find out of the puppy is still destroying the house.


See if that potential client and the person who you referred them to connected in some way. To see how a past client is doing without you.

Simply fire off one line emails saying “I hope all is well. I just thought I’d pop in and see how everything is.” These can go a long way in opening lines of communications. Most times there may not be a response. But when there is it usually opens the doors to new opportunities.

When I stopped making the mistake of not following up, I found myself landing a few clients as well as getting some Christmas gifts and cards. Remember business is about the relationships of people. People react to people caring. If you show that you care it will come back to you in the long run.

Respect Time

Finally, time. I’m all about time. Money comes and goes, but time is truly our only asset. It’s the one thing that no matter how hard we try we can’t create more of. It’s something we never get back.

Respecting your clients time is things like when you schedule a 30 minute call, making sure that you cover what you need to cover in that 30 minutes or less. It’s also things like not waiting until the night before a launch to tell your client that you don’t have everything you need to launch.

Respecting your own time is essential too. Remember the office hours I mentioned earlier. If your clients don’t respect them and call you on your day of no calls and you pick up, then you aren’t respecting your own time. Another thing that freelancers do is answer emails “off-hours” at night. If you stop working at 6pm, then stop working. Spend time with your family. Go for a bike ride. Whatever it is, but don’t do work. Respect that time.

If you do want to work and answer emails then use a tool like Boomerang to schedule emails to go out the next day. If you send an email to a client at 10pm, they will remember that and almost think that you will be working then.

I’ve made my fair share of mistakes, and probably will continue to do so. Just ask my wife. However what I hope that you get from this is an insight into some of the mistakes that I have made during my freelance career and don’t make them in yours.

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I know we don’t like to share our faults too often, but this list is by no means comprehensive, it’s one that I’ve made based around myself. I’d love to hear in the comments some mistakes you’ve made. Sharing our faults and what we’ve learned from them to fix them is how we grow not just our businesses but as people.

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