Sales is one of the most challenging yet rewarding careers that you can have. I have been in sales my entire career and I absolutely love it. But it wasn’t always like that. Sales is a hard career to be successful in and I have had my struggles. There are usually many ups and downs that can be discouraging to many people starting out but if you have what it takes it can be a great career choice. So let’s see if you have it!

I have always loved being in sales but it has not always been easy. In fact, it can be overwhelming when you first start your sales career. Find out what some successful sales reps had to say about that in a bit. But if you can survive the first couple of months and have the skills that it takes you can make a great income! So let’s find out if you have what it takes!

Why Is Sales Hard?

Sales is one of the best careers available for many reasons. But is Sales hard? Absolutely. It doesn’t mean that it is hard for everybody. I have seen new reps catch on quickly and take off in their first few months. But that is the exception and not the rule. For the most part it takes time for someone new to sales to get used to the process which takes some skill and a lot of practice. So why is it so hard for most reps? Most sales jobs are commission based and when it takes you a few months to make some sales and get paid that is a pretty big challenge for most of us. Most companies will give you a 3-6 month period where they may give you a small base salary or a draw but most of the time it is not enough. So you end up struggling for a while before you can get your feet under you.

Most sales jobs are not 9-5 which means you will work hard in the beginning. And will need to take your work home with you as well. Whether you are practicing your pitch or preparing for your week, you will find that there just isn’t enough time in the day to get done what you need to.

When I first started out in sales I was young and single so I was able to live off a minimal wage and could work as much as I wanted to. But over the years as you change jobs that becomes much harder. If you are married and have a family it can be challenging to balance your work life and family life. It is also much harder financially. Especially if you are a divorced single father with child support due no matter what. If you are older when you first get into sales you definitely need to carefully plan out your options to make sure you can make for at least 3-6 months on minimal income.

There is your schedule as well. Many sales jobs have appointments all over your territory and some evening appointments as well. I know many reps over my years that struggled with not being home every night and having to travel. But here is the deal, most sales jobs will require both of those so you will need to be prepared.

What are the Hardest Types of Sales Jobs?

There are many different types of Sales Jobs available and some are harder than others. I would say the hardest type of sales job is In Home Sales. This is where you or your company sets up an appointment to go to the potential customers home to do a product demo or a presentation. For most people that is very intimidating and very awkward. Which it is. There are only a small percentage of sales reps that have the skills to be successful in In Home Sales.

Outside sales in general is one of the hardest types of sales jobs. Coincidentally, it is also where you can make the most money! But there is a good reason for that. To be honest, most outside sales people fail and choose to do something else. That doesn’t mean that you are a bad person and are a failure. It just means that Outside Sales is hard.

So what makes Outside Sales so hard? In most Outside Sales positions you will be responsible for bringing in new clients and that means cold calling! And it takes a special talent to cold call and be good at it. Cold Calling is probably the number one reason why people don’t like sales. And for good reason! It takes discipline that many people don’t have. I have been in sales for 30 years and have seen many new reps come and go. I would say that only 25% of people that try outside sales are successful.

Another hard type of sales is Insurance sales. Have you ever noticed if you look on Craigslist for sales jobs that there are a million Insurance Agent listings? Because it is so hard to last long enough to make money. If you are young and think you might like sales that would be the time to try insurance sales. You will need to live on minimal income for about a year. But the good news is that if you can stick it out for a year and you have some success, your commissions and residuals can be fantastic! I have a friend that is very successful in Trucking Insurance and he loves it.

Those are probably the 3 hardest types of sales out there. There are many types of sales jobs to choose from and they all present challenges but I needed to narrow it down and I think that is pretty accurate.

What is the Hardest Part of Sales?

This probably depends sales reps individually. Everyone has different skill sets but they usually struggle with at least one part of the sale. Here is the sales process for some guidance. I wrote another article specifically on the sales process and you can find it here.

In my 30 years of experience I would have to say that closing the sale and handling objections is usually the part that reps struggle with the most. The fact is that asking someone to spend 10K, 20K, or 50K can be a little unnerving. I remember the first time I asked for my first sale over 30K I thought I was going to have a nervous breakdown! And this is why most sales reps don’t even ask for the sale. They just say that they will send them some more information and follow up. ASK for the SALE!

Now that doesn’t mean you can’t struggle with other parts of the process. I have lots of example over my career. Oddly enough, I have know people that have know problem asking for the sale but struggle with the warm up. They always want to get right to the presentation. Which is great….but you can’t forget the first few steps or you can lose your potential client in the beginning. If they feel like you have no interest in them then forget it. You have already lost.

The presentation can also be challenging but usually with enough practice you can get better at that. The main issue that reps struggle with, especially new sales reps, is that they want to read the presentation like a script because they have memorized every part it. The key to a successful presentation is to give it in conversation form. That way you are getting your potential customer engaged and more engaged prospect is more apt to by what you are selling.

Your First Months in Sales

The first months can be very overwhelming for new sales reps. There is so much to learn and so much to get used to. You really don’t even know what to expect as you go through your first couple of months. I remember my very first sales job right out of college. I remember thinking wow this was not what we talked about in my interview. The truth is, it is hard for even the best sales manager to help new reps understand the job.

What I usually find the most helpful is to try and find someone on your sales team that you relate to and ask them for help. Ask them about their typical day and what not to do. And you are not really looking for the best sales rep on your team at this point. In fact, that person might be the least willing to help you any way in the beginning. You want to find someone that will be easy to talk to so you can ask them lots of questions. I know that I used to ask so many questions they probably felt like pushing me off of a cliff sometimes. But that is the best way to learn what you need to learn.

Usually your manager won’t expect much from you for the first few months so take that time to learn as much as you can. And to practice as much as you can. Again, find someone that you feel comfortable with and ask them to role play a little with you. If you are being proactive in some of those steps your manager will notice and they will be more apt to help you as well. You will also want to do as many ride alongs as possible. Most sales reps hate doing ride alongs with new reps but ask your manager to help set some up. This is where I always learned the most. And here is a tip. Make sure to ask the rep you are riding along with to just do it like they would normally do it and not like your manager wants it done. This will make them more comfortable and more willing to do more of them with you.