One Big Clue That You’re Ready to Outsource and How to Start

Jenna Kutcher 

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September 18, 2019


ready to outsource


When I was a solopreneur, the idea of outsourcing made me seize up with anxiety. I was working around the clock to maintain and expand my business, and the thought of bringing in someone else to my perfectly orchestrated system that wasn’t broken made me a little woozy, if I’m really being honest. But I went into business for the freedom and flexibility of working for myself, and instead I found myself a slave to the calendar and my clients rather than being free and living my best life.

I have a feeling you might be experiencing something similar. Whatever category of business you’re in, when you’re the one running the show, it can feel impossible to hand over even a little bit of the reigns. Maybe it’s that you don’t have time to train someone in, maybe you don’t want them to see your system, maybe it’s a finances thing, or maybe you just don’t trust anyone else with your “baby”.

I get it because I’ve felt ALL of these emotions. It’s okay to lay down your fears about money and time and control to allow people to come in and lend you a hand. In fact, it’s GOOD for you. Let me spend this episode walking you through it, so no matter WHAT it is that is holding you back, by the time you reach the end of it, you’ll have clarity for what your first hire should be for when you’re ready.

I’ll share details about when to outsource, how to find the right help, what to look for in new hires, how to cost it out, and mindsets around time vs. money, and which one you should consider a more important currency.

How I Knew

I didn’t know I needed help until it was almost too late. I always feel a pit in my stomach when I think about this season of life because it was DARK. I was a solo-preneur, on my own, and we had just found out we were pregnant. I was shooting 30 weddings and was at the peak of my career in terms of profits, bookings, all the things…. And then we found out our baby didn’t have a heartbeat and it was all threatened.

For the first time I didn’t care about email, social media felt so silly, every ounce of hustle and productivity was swallowed by grief and I finally realized that I had built a business that stopped the second I stopped. I didn’t have a system, I didn’t have a team, I HAD to show up, even when life begged me to just stop and be. Because when I didn’t, everything would be gone. I made my first hire in that dark season and finally started to see the light. I knew that while I disconnected, my clients were being loved on, being responded to, and that my business was still running without me.

It was the first dose of freedom that became my obsession. The girl that had turned down the offers for help in the form of a virtual assistant 3 times was now looking to hire more help, to get more hands on deck. That tiny feeling of freedom has fueled me from that day in 2016 and has led me to today where I have a full team of salaried team members and trusted contractors that are running my business while I’m on vacation with my family on the other side of the world. So let’s talk about how I got from there to here… shall we?

What Do You Feel Guilty About?

If you don’t think you need help, then let’s start here: What things do you apologize for or feeling guilty about?

Outsourcing doesn’t always start within your business. Rather than thinking about what you spend most of your time doing — those things that you LOVE, start to consider what you spend most of your time apologizing for or feeling guilty about.

Like actually start to pay attention to the words that follow “I’m sorry” that you’re saying in your daily life. I’m sorry the laundry isn’t done. I’m sorry we have no food for dinner. I’m sorry I didn’t get back to your email. I’m sorry I’m late on the deadline. I’m sorry I didn’t write that post. Catch my drift here?

What you’re saying sorry for is a huge barometer in terms of where you actually need help. It’s those things that make us feel stressed/anxious/flustered — like we’re not doing enough, THOSE THINGS. So pay attention to the apologetic statements coming out of your mouth, it’s the best way to figure out where exactly you need support.

Identify the Biggest Pain Point

Pick the biggest one first, and get help with that. And then keep getting help with the next biggest thing, and the next, and the next. It doesn’t have to be paid help, either, it can be help from family, friends, your partner or spouse. Sometimes it takes pinpointing the help you need and then communicating it to help ease up your workload and reshape your priorities.

If we’re talking biz, when it comes to entrepreneurship, a great place to start is by hiring a virtual assistant or VA. There are so many types of VAs out there who can help you with social media, invoicing, emails, calendar management, content writing, and so much more — really, whatever you need help with the most. Many VAs get into that line of work because they’re highly detail and task oriented individuals. They take direction well and enjoy being in a support role to allow you to free up some of your time and take back some of your life.

If you paid someone $20 an hour to work on some of your biggest pain points for a few hours a week, would it be worth it? Would those things you always procrastinate or put off to the end of your to-do list be better utilized if they were a ball in someone else’s court who actually enjoyed and excelled at them? I mean, that’s a game changer if you really think about the time and energy you could be saving with a small, simple shift to outsource to a VA.

I remember when I hired my first VA Caitlyn – who is still on my team today – the expense was equivalent to the mortgage we were paying and IT HURT. BUT I did the math and realized that with the 40 hours she would save me the month, all I had to do was book 2 more photo shoots to pay for her and those would take me max 10 hours, so it would save me 30 hours a month spent doing the tasks I hated so that I could focus on what I was really really good at and she could do the things she loved. It was a win, win, win, and after about 2 weeks, I knew that I had made the right call.

Focus on Your Genius

Going into this year as a new mom, I took a good hard look at my business and how I was spending my days. Out of the 30 or so tasks I found myself doing on a weekly basis, there were only 3 places that couldn’t be outsourced. THREE. The vision of the business, the voice on the podcast, the face in the pictures.

That’s literally it. In ALL the places I can serve my business, with ALL the hats I CAN wear, I only need to be doing these 3 things and every single other thing can and should be outsourced if I truly want to free up my time.

So I want you to really think about a couple things. What are the tasks in your business that come to you really naturally, without much strain or pain or effort? What are the things that you LOVE to do, that light you up, make you feel alive, and give you a sense of deeper meaning and purpose? I want you to really get specific, and maybe even write down what those are.

Now let’s work through the trouble zones or the things that are likely the last to get done because you dread them the most. Write down every single task and pain point and the work that falls outside of those genius spots that you deal with on a daily or weekly basis. These are the things that in many ways drain your energy, take more time than it should, don’t get done, and don’t even fulfill you all that much. It’s really powerful to realize that those tasks that don’t come natural to you DO come natural to someone else.

It’s going to look a little different for everyone based on the positions you hire and how much work they’re doing, or where you’re getting help, but no matter what, having help in place to do the things you dread is going to give you a significant slice of your time and freedom back. Odds are, when you’re focusing on the things that YOU’RE really, really good at, the investment will pay off immensely and you’ll feel a whole lot happier in the meantime.

Where to Find Good Help

This might be the most intimidating part of the process, but I approach hiring from a way less complicated, less daunting standpoint, so hopefully I can shed some light.

There are so many resources available for finding help, and when it comes to outsourcing, it’s best to first figure out what you need most. Regardless of whether you choose to outsource professional tasks or personal tasks first, my number one tip for finding a great VA, home cleaner, yard person, nanny, accountant, or whoever else it is that you need, is to ask around.

Yep, I’m going old school with this advice. But it’s so true that people can present themselves as one thing online or on their resumes, but it’s so much more powerful to get a personal recommendation. Ask the people in your life who you trust or who you see are killing the game. If you have friends who are entrepreneurs, ask them where they found their teams or if their contractors have any openings. Ask your neighbors, friends, and local family members if they know of service providers in town who are trustworthy and quality professionals.

And a great extension of word of mouth these days is utilizing social media and online groups. You can also join Facebook groups with like-minded individuals or businesses in a similar industry as yours. The Goal Digger Insiders Facebook group is constantly opening up conversations about hiring, outsourcing, and what to look for when you’re ready to hire. There are so many business owners and VAs and social media managers and more on there with tons of advice and know-how that they’re always dishing up to other community members.

Finally, you can also take advantage of platforms that match you with potential team members. LinkedIn, Upwork and Outsourcely are all platforms for business owners and freelancers of all kinds to meet, collaborate, and build lasting work partnerships. You can find all kinds of remote workers on there, including VAs, writers, coders, graphic designers, website designers, and much more.

Keys to a Strong Job Posting

I would recommend getting HYPER specific in your job posting. Be sure to include exactly what you’re looking for in an individual and why, whether you need someone highly detail oriented or creative or who has experience with SEO or small business accounting. Get really in depth with your vetting questions and ask for people to share what makes them stand out, what would make them a good fit for your brand, and how they could impact your business.

A lot of times, even with these online services, you’ll be able to instinctually tell who is being phony and who legitimately cares about your job posting and the opportunity at hand. Ask some questions, get recommendations if you need them, and make sure you actually LIKE them — You’ll want to interview them or at least vet the experience and look into their background to some extent. Pay attention to the way they describe themselves, the way they communicate, how they speak about your brand and if it’s aligned with your vision and where they see themselves going.

There’s a lot of generic hiring lingo out there that people use just to seem professional, but you want to be looking for people whose genius areas are within the needs you’ve identified that you’re hiring for. Look for people who are enthusiastic and on fire for what they do. Look for the ones who are invested in learning more about their industry, exploring new opportunities, and who want to grow with you. Look for eagerness, passion, and excitement.

Each time I’ve hired, I’ve posted the job posting, shared it on social, and made a decision and hire within 5 days. I move fast, I follow my gut, and I get things moving quickly. Once I’ve found my person, I move on — it’s like wedding dress shopping, once you pick yours out, stop looking for others. Make your decision and get to work.

We are all a whole lot more intuitive that we could ever imagine, and when it comes to hiring, it’s often fairly evident who the right fit for your management style and brand is from the jump. Don’t be afraid to listen to that instinct. I’ve been known to hire people in less than a day because I loved their online presence, they had legit experience that vibed with my brand and voice, they had sound, actionable feedback for my brand and I just liked them as people. Following that instinct is a whole lot more important than doing what you “think” you should be doing when it comes to hiring and following a three-interview, two project tests, and a reference check like your friend told you to do.

The Big Picture

Your business deserves to reach its fullest potential, and you deserve to not be a slave to time. Getting help is the surest, and fastest, way to achieving both of those worthy goals. Outsourcing is a life-changing shift to be able to get more out of work and life, and I can’t wait to see how you do it, how you release the grip of control and money and open your hands to freedom and possibility — the two reasons you started this whole thing in the first place, right? Press play on the episode above for the full discussion on if you’re ready to outsource and more help to begin your outsourcing journey.

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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