How to Decide if You Should Hire Your First Employee

By Sean Ogle •  Updated: 09/22/15 •  9 min read

Have you ever felt like something you’re working on has a ton of potential, but hasn’t been fully reaching it?

That’s how I feel about Location 180.

Over the last 6 years we’ve built an incredible community here, but the potential for more is so much greater.

I’ve been fully engrained in the life of a solopreneur for years now. I built a business that allows me to do the things I want to do, when I want to do them.

And at times, for better or worse, that’s meant I haven’t grown the business as much as I could have.

I’d play instead of work. I’d travel and maintain, rather than stay and grind. Delay rather than ship.

With the amount of golf I play, you might think I was a 30 year old retiree! And while I’m fortunate to be in that situation, I’ve let things stagnate that deserve to be cultivated.

I’ve thought a lot this year about why this is the case.

And the answer has become pretty clear lately: I need help.

It’s really that simple. There are tasks and projects I haven’t done, simply because I don’t have the bandwidth to do them.

This allows me to maintain the business where it is and grow it a little bit year over year – but it doesn’t allow me to propel it forward to a place where I can help even more people.

Liz Froment has helped me out on the side for the last three years. She’s been the community manager for Location Rebel, and has helped with some social media for L180 among other things.

This summer I’ve realized that she is the key I’ve been missing.

I’ve been needing someone who can help me take ideas and turn them into action. Someone who can pick up the slack on tasks I have trouble completing. Someone who has a stake in the business, and is just as motivated as I am to grow it.

Liz is that person, and I’m incredibly excited to start working with her more closely and making her a more integral part of Location 180 and Location Rebel.

But as a soloepreneur or lifestyle entrepreneur, how do you know when the time is right for you to hire your first team member or employee?

There are a lot of factors, and making that financial commitment can be really scary. It doesn’t have to be though, by going through and having responses to the following questions you’ll have a much clearer idea of whether or not you should bring on some extra help.

By the end of this post, you should have a much clearer idea of whether or not you should hire someone to help you with your business – and if you’re not ready, understand what you need to work on to get to that point.

1) Are you having to ditch projects with potential simply because you don’t have time to work on them?

Not having enough time doesn’t need to be your excuse for not pursuing a worthy project. You certainly need to pick and choose which things will be most valuable to your business, but if you have some extra help, you can more easily create multiple revenue streams or projects simultaneously, which will fuel growth.

If you’re just getting started, it’s in your best interest to focus on one thing. I spent the last three years making Location Rebel my primary paid product, and it grew quickly because of that focus.

However having someone else to help with some ancillary products to expand our offerings makes sense at this point.

Action: Make a “Pursue or Pass” decision for everything.

Are those ideas you’ve been sitting on for a year not happening because you don’t have time, or are you just not that excited about them? Make a pursue or pass decision on all of the things you have floating out there.

Add dates and timelines to each.

From there, assess which one(s) you’d be able to do if it were just you, and what else you could do with outside help.

2) Can you clearly articulate exactly what needs to get done?

If you don’t have a plan in place for your business, hiring an assistant could be a huge waste of time and money. You should have a clear vision of what needs to get done, and then hire someone who can help you execute on that vision.

For me, I’ve got a clear long term vision, but Liz has been instrumental at helping me work through the day to day of making it happen.

Action: Create Your Strategic Plan (See #3)

3) Does your business have an overarching strategic plan in place?

I’ve struggled with this. I’ve taken a very reactive approach to Location 180, rather than truly taking the time to plan out what the future is going to look like.

When you don’t have a plan in place, it’s nearly impossible to effectively delegate to someone else. So make sure you have a solid idea of where things are going, and then you can pass of tasks, or even better, collaboratively work together on the future of the business.

Action: Start creating your strategic plan

This should be a whole post to itself, but some key things to think about are:

By understanding these fundamentals, you’ll be in a better place to bring someone else on board to help.

4) Do you have a clear idea of how hiring someone will make you more money?

If you’re going to spend the money to bring someone else on board, it should be a decision that helps make the business more money.

The last thing you want to do is spend a chunk of your monthly revenue and see sales and income remain stagnant.

So answer this question: “How will hiring someone grow your business?”

For me the answer is accountability. I’ve known what needs to be done for a long time, but I haven’t held myself accountable for doing it. Having Liz to help me stay on track and actually get shit done means we’re shipping more often, and setting up the proper systems to facilitate growth – which should lead to more revenue.

Action: Analyze Your Income Stream(s)

How are you making money right now? Will hiring someone expand those current revenue streams? Allow you to create new ones? Both?

Know where the money is coming from, and where you’d like it to be coming from in the future.

5) Do you have tasks that you dread doing? So much so that they aren’t getting done?

It doesn’t matter what level of business you’re in, there are going to be things you don’t want to do.

Sometimes you just deal with it, get them done, and move on.

Other times, you put them off, put them off some more, and they never get accomplished.

This can lead to huge delays and missed opportunities.

For instance, I have a product that has been done for awhile, but hasn’t been released because I haven’t wanted to go through the editing process.

How easy is it to hire an editor to do it for me? Extremely, but I just hadn’t done it until recently.

Don’t let this dread be your excuse for not getting things done.

Action: List out all the things you hate doing.

Sometimes you just block out the things you don’t want to do. Instead of that, list them all out, and then analyze the best way to hand them over to someone else.

If the list is extensive, this is a great indicator of you needing some extra help.

6) Do you have a good reason for not hiring someone?

The responsibility that comes with hiring someone can be scary. For me, I was afraid of the uncertainty of what would happen if things didn’t work out.

I’ve taken a lot of risks in my life, but I still have a difficult time investing in my business. To grow it, that has to change.

So why haven’t you done it yet? Afraid of the money? Afraid of losing control? Afraid of having to support someone else?

Action: Analyze the why. 

If you can understand the hesitation behind the decision, it makes it easier to plan for all the things that could go wrong, which will give you peace of mind in confidence in your decision.

7) Do you have positive cash flow?

If you’re a solopreneur and not making any money, the last thing you want to do is bring on more financial burden and hire someone else.

Is your business making money and is it cash flow positive? If so, good! You could be in a good spot to hire help. If not, what’s the fast way to get there?

Action: Think through the business fundamentals and work on them first.

What are the business fundamentals?

So, should you hire your first employee?

That decision is up to you to figure out, but if you answered yes to most of these questions then there’s a good chance you’re at a point where bringing someone else on board will be beneficial.

Bottom line, if you’ve got money coming in, you’re putting off doing things because you don’t have the bandwidth, and you have a clear vision for the future of your business, a full or part-time employee can make a world of difference.

Not to mention having someone to talk to at the virtual water cooler is a nice change of pace from being totally on your own.

Have you wrestled with this decision before? What did you do? What were the deciding factors in making your decision? Let us know in the comments!


Image Credit: Jigsaw from BigStock

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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8 comments on "How to Decide if You Should Hire Your First Employee"

  1. Alex Swallow says:

    Thanks for the great advice Sean and congratulations on the continued success of your business.

    Good luck to Liz as well!

  2. John J says:

    This is such a well written article. It makes me realize right off. I need to create a more organized system for my self. I don’t believe I ever leave your blog feeling as though I haven’t gained something for my time spent reading. Keep up the good content.

  3. benay says:

    Thanks Sean. I’ve already hired a few staff who are just amazing, but it took lots of trial and error (i.e. people who did not work out) to get here. Now, just about ready to hire again so I read your article from that perspective. Still quite helpful. i look forward to reading more about how you do your strategic planning. Keep up the brilliant work – B

  4. Leslie says:

    Hi Sean,

    This is an excellent article for any business owner. Creating a strategic plan, finding ways to do what needs to be done (even if you’re not the one doing it), creating your streams of income and making sure there is a positive cash flow are the building blocks to any solid business.

  5. Hello there, Sean! A friend shared this article with me and I’m so glad that she did! I’m an online business manager, and wanted to point out that these questions apply to outsourcing to freelancers as well! These are the same sorts of questions I ask my clients before agreeing to partner with them, and those clients who are clear on the answers before we begin our work together always see a larger and faster return on their investment. It’s a head start, if you will…

    Help in your biz doesn’t HAVE to come from an employee – and hiring virtual business assistance can be a great way to dip your toe in the “delegation pool,” so to speak… Doing so helps you create and document procedures so that when your business can and does indicate a need for an employee, you have the documentation to recruit, hire, and evaluate the “new guy.” Sounds like Liz is tried and tested so you’re way ahead of the game!

    Thrilled to have found your blog and follow your adventures!

  6. Such a great post, and so timely for me, too. Just hired an assistant to take a huge chunk of work off my plate so I can focus more on what fires me up and makes me money.

    Asking myself these questions confirmed that I am making the right choice. Feeling good about delegating and taking this next big step in my business!! 🙂

  7. Gustavo Sims says:

    I am looking forward to hire an employee this month. Thank you Sean for your suggestions. Keep up the good work.

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