This post may contain affiliate links. As an affiliate partner of various brands, we may earn a small commission on qualifying purchases, at no extra cost to our readers.  That said, we will only recommend what we trust and know.

So you’ve taken the leap to start your own business to support yourself abroad or you’ve transitioned into entrepreneurship while abroad. Things are going well, you have clients and you’re making money. If you’re currently a team of one or a ‘solopreneur’ you’ve also probably hit a wall with your productivity and efficiency. Let’s face it, you can only do everything yourself for a limited amount of time. Youtube is a wonderful resource, but you just might have hit the point in your business where not only could your time be better spent doing other things (than watching YouTube tutorials), but it’s actually costing you money doing everything yourself. 

This is an obstacle that so many entrepreneurs encounter and to be frank will continue to face throughout their entrepreneurial journey: to hire help or continue doing it yourself? That is the question.

Oftentimes, it’s not that entrepreneurs don’t know they need help, it’s that they have become accustomed to the constant labor and busyness of solopreneurship. Jumping from Canva to Quickbooks to Calendly to Zoom over and over again throughout the day. However, even if you’re the most staunch, lean mean solopreneur machine, you will come to a point where you recognize that you are in fact the bottleneck in your company. 

No amount of all-nighters, TikTok hacks, or Instagram inspirational quotes will help. It’s a hard pill for you to swallow, acknowledging that your performance (outside of your zone of genius or core competencies)  is now having a substantial negative impact on your business performance.  Whether it be the delivery of your services, the lack of systemized workflow to maintain efficiency and product quality, or the inconsistency of your marketing endeavors, something has to change.

You will need to hire someone to help you. Perhaps the fact that your business is bringing in enough revenue to reinvest in its growth is exhilarating for you and you can’t wait to hire help. Or perhaps, you’ve become entrenched in the solopreneur mindset of “I’ll figure it out” or “I’ll just do it myself.” Although both mindsets are really critical for fledgling businesses, it’s time to grow some other key entrepreneur muscles’. Mainly discernment, communication, and intuition. And the sooner you can get your reps in, the sooner you will experience the business growth you’ve been desiring. 

So how do you invest in expertise, especially if you have a business with global reach?

Red and white Help Wanted Sign on store window.
Image: iStock

For most solopreneurs, this can be a very scary and overwhelming undertaking. Or you might just feel skeptical. Perhaps the thought of hiring someone is bringing up your unhealed trust issues (lucky you, not just reserved for familial and romantic relationships).  How can you trust that people are actually going to do what they say they’re going to do? How can you ensure that you’re going to like the end product or result?  That overwhelming feeling of uncertainty (and need for guarantees) may cause you to reconsider if you should really invest in your business or if you’re even ready since you’re feeling so unsure. 

Saving for a rainy day is hardly an exercise I’d deter any entrepreneur from doing, however there are ways to go about hiring help, a contractor and even an employee that mitigates the risk of investing in the wrong service provider or even in the wrong service for your business. 

To be honest, in order for any business to grow you will have to invest in that business whether it be investing in human capital with a contractor and employee as needed in your business, or investing in software or utilizing more software to help streamline your business. All of this requires money.

An adage I share with clients and often cling to myself is, “scared money don’t make no money.” Growth does require an investment. With all investments we want to do our due diligence and I also want you to make sure you are mindful of your aim and what an acceptable return on our investment would look like. Simply put, you must first define what success or money well spent would look like for you. 

Sometimes the return on investment doesn’t automatically equate to sales and revenue, but it may equate to efficiency (freeing you up to do more business growth activities), or it may equate to peace of mind (knowing that your bookkeeping or accounting is being done properly may result in less anxiety, and more restful sleep or actual sleep in the first place). It also may equate to systemization through automation, thereby allowing you to handle more volume, be it interest from prospective clients to disseminating freebies, to nurturing your community across social media channels more consistently, while utilizing fewer resources.

Here are some tips to help you embark on a successful hiring journey:

Review Labor Laws and Tax Implications

Understand how you can engage with a contractor or hire an employee while abroad. The labor laws that govern who is considered a contractor vs an employee may depend upon the country where your business is registered, where you conduct your business and which countries your contractor or employee may be from. 

This is also important when considering how you can pay them (are there any minimum wage laws you need to adhere to) and if you’re obligated to provide any additional employee benefits. You would definitely want to consult with your accountant(s) to see if there are certain forms that need to be filled out on the contractor side so you can write off that payment as a business expense. Your accountant(s)  should be able to guide you as to whether you may have to take a further step and consult a labor lawyer, especially if you intend to hire a full time employee.

Identify What Needs To Be Done

How do you create a job description that actually attracts strong qualified talent? In my opinion,  in order to attract the ‘right’ contractor and not end up regretting your decision or second-guessing this business investment, it is crucial that you really understand what you’re looking for in a contractor. 

Write down all the things you need done in your business. Then from that list circle all the things you don’t like doing, then ‘star’ the things you are not really good at. For example, you may enjoy making your own graphics in Canva, but if it’s taking you a whole day to create them, then you’d probably be better off letting someone else take over.

Next, prioritize each list (the things you don’t like doing and the things you are not really good at) and rank them either by what you think will bring in more leads and maybe potentially more sales for your business or by what is going to alleviate some stress for you. Truly this prioritization should be in alignment with your current day-to-day business goals with an eye toward the next three months of your business.

Note: Feel free to prioritize your peace as well! If there is an aspect of your business that is causing you resentment and because of this resentment a bottleneck is forming, prioritize alleviating this pain point even if it does not directly lead to more sales, because a happier, less-stressed business owner will have the mental and emotional bandwidth to bring in more sales. 

Know your current workflow. Your next step is to outline your current workflow. Workflow simply refers to how you do the things you do. For instance, when you launch a product what are the tasks you complete to launch the product? In what order? If you create social media content, how do you come up with the ideas? Perhaps, first, you create a content calendar that focuses on one of your business’ content pillars, then you consider what promotions you may have during that particular month or quarter, then you design fifteen static image inspiration posts, five static quote posts, five educational reels and five inspirational reels. You would want to outline how you source images, what types of images are in alignment with your brand (especially if you don’t have a brand guide with your colors, fonts, emotions, definite yes/definite no already articulated).

You’ll also want to articulate what software you use, and how you use it. For example, if you use Google Drive to store your product images, you’ll want to write down how you store the images (any naming standards) when they’re uploaded, or what happens once they’re used. 

This may seem like a lot, and it is! As a solopreneur, you probably don’t realize how much institutional knowledge you have floating in your head. It’s important for you to articulate as much of it as possible, so that you can accurately write a job description based on your actual business habits and needs, but also because people can’t read your mind. Even a well-written job description complete with an articulated onboarding document or process that goes over how you currently do things and why or how you like things done will still leave room for interpretation and frustration. We’re all human and can interpret instructions differently. You close the gap on miscommunication and mitigate the amount of time to onboard a contractor when you have clarity as to what you do, what your aim is and you have the ability to articulate it succinctly. Confusion in business usually leads to a no or a loss in a potential sale, but confusion in business also leads to time and money wasted in hiring the wrong person or having to onboard for much longer. 

Black male businessman writing next to open laptop on desk.
Image: iStock

Write down the frustrations you have with your current processes. Reflect on your current systems and workflows and write down all the instances where the workflow is tedious or disappointing. Write down what your ideal workflow would do and what you’d expect the ideal workflow to resolve, either technically or emotionally within your business. As business owners and service providers, we sell on emotion – the emotion of the transformation our product or service provides. This works in reverse as well, an aspect of you feeling as if the investment in hiring a contractor is money well spent, is emotional.

How the process makes you feel, how the transformation resolves feelings of frustration, stagnation, uncertainty, angst and so on. Being able to articulate the tasks that are tedious, your current method of completing the task, and also how it makes you feel, and how you hope to work with someone who will get the task done and implement a more efficient workflow, will make you feel better. Ultimately, you want to feel good paying someone to help you. The value they bring to your life and business makes you feel good spending money on their services. 


Craft a Strong Job Description

Search for a basic job description for the position you want to fill. Utilize a google search to find a basic description with the basic requirements and typical responsibilities of the position you want to fill, be it bookkeeper, social media manager or graphic designer. Then infuse the basic description with your specific pain points, a brief outline of your workflow, your current frustrations, and what success would look like to you.

Once you create your job description it’s important you place it somewhere people can find it. I have made the mistake of writing a job description and putting it in a generic digital Nomads group and getting all types of absolute nonsense in return. I got way better results by putting my job descriptions on freelance-specific job boards.

Young black businessman working on laptop
Image: iStock

Figure out the Pay Structure

Money is usually a touchy subject and I think solopreneurs often encounter the interesting dichotomy between paying someone to do a task that you’ve been doing ‘for free’. However, everything has a cost, it’s why ‘sweat equity’ exists. I find a lot of solopreneurs get hung up on costs but you have to remember we’re thinking about our return on investment and if we think about it in those terms then we can start really considering if I pay someone $300 or $1,000 to get this done, how will that free up my time, lead to more sales and eventually pay for itself. And perhaps that is how you should frame it when you’re deciding on which tasks you hire a contractor for first. It should be the tasks that can pay for themselves quickly and/or eventually. For example, setting up email sequences, finding someone to do your newsletter, and finding someone to manage your social media to get more people to your website. Expertise level will also impact salary. If you are looking for an expert, that’s going to cost more money than an entry-level person. 

Start the Interview Process

It’s vital you understand your non-negotiables so you don’t have to interview five million people to fill a position. Some things to ask for and review before the interview: link to their website or portfolio, any relevant case studies with the appropriate analytics showcasing the tangible effects of their work. What time zone do they live in and what are their working hours? How well do they work autonomously and remotely and if they can give an example of that? Which project management tools do they utilize, their preferred methods of communication and how well do they handle criticism/request for revisions?

Once you digest all of the responses to your job description and the pre-interview questions, then it’s about scheduling the interview. You’ll be looking for alignment in work values and also, to a certain extent, chemistry. I strongly recommend identifying a probation period of time or probation project in order to fully understand whether or not you will be able to work together. 

Monitor and Manage

Once you have hired someone for the job it’s not over. You have to monitor their work and you need to really understand that maybe the first few people you hire may not be a good fit for some reason or another. Be patient with yourself and extend yourself grace. Understand you are learning on the job. This is an excellent opportunity to examine how you communicate and how you articulate your business messaging and how well you manage people.

It’s also a really good time to reflect on other business necessities. Maybe you need to develop (or hire someone to develop) a brand voice guide and messaging points in order to expedite onboarding for future hires.

With all that being said, hiring as a solopreneur can be extremely frustrating and nerve-wracking, but if it is done intentionally and if you do your due diligence, it can be a game-changer. It can be an amazing opportunity for exponential growth in your business and an amazing return on investment. It is also inevitable; in order to have any sort of work-life balance, to really enjoy your work and to cultivate a life well lived abroad, you’re going to need support, you’re going to have to trust people and lean on others.

Originally posted on our sister site, the Roaming Pro on October 3nd, 2022.

Skip to content