025: An Entrepreneur’s Guide to Outsourcing

With Kelly Lawson

As a solopreneur, I was used to being a party of one. I started and grew my business all by my lonesome. The thought of outsourcing some of my ever-increasing workload made me incredibly anxious. 

So you know what I used to do? It all. I. Did. It. All. Most days, I worked around the clock to do ALL OF THE THINGS required to run the photography side of my business while also burning the midnight oil to grow the digital side. It was a straight-up recipe for exhaustion. But somehow I couldn’t let go. 

The idea of letting someone else into my complex system made me extremely skittish. 

Plus, I didn’t have time for that! I was already working non-stop. The thought of having to stop what I was doing to recruit and hire another human overwhelmed me. And then I stressed about the time it would take to train them on the things that were up in my head, all of the backend processes and the wacky systems I had developed that only I knew. 

BUT, then again, on the other hand… I was reaching a breaking point. 

I mean, the whole reason I had left my career for the land of entrepreneurship was to bask in its freedom and flexibility. And yet, somehow, here I was, stretched so thin, working all hours, juggling so many tasks, being controlled by my calendar and only finding time to work on growing my business in those little in-between moments. And even they were becoming more and more rare. 

This was NOT what I had envisioned. 

I felt ripped off. Duped even.

Why did I leave a stable, well-paying career for this? Things were not progressing as planned. And I was getting more burnt out by the day. 

So, maybe you know that feeling, too? Maybe you can relate? To when little tasks start to feel like giant hurdles. When your life starts to feel like an ever-accelerating hamster wheel? 

It was like that Talking Heads song: How did I get here? 

If any of this sounds familiar, that’s ok. Because there is a way out. It doesn’t have to be like this. You know what I’m talking about – those late nights hunched over your laptop. The weekends consumed by work? 

My friend, these things are simply a sign. A red flag that you need help. And the great news is that it is easier than ever to find talented peeps to pitch in, so you can focus on the bigger things and preserve your sanity and health in the process, too.

I’m going to spend this episode walking you through outsourcing, no matter WHAT it is that’s holding you back, so that, by the time you reach the end of the podcast, you’ll know when you’re ready for your first hire. You’ll also know what to look for in a new team member, or a contractor. And I’ll tell you how to run the numbers and throw in some mindset shifts that you will need to get comfy with in order to start valuing your time over your dollars. Okay. You ready? Let’s do this.

In this episode, we talk about:

  • Keeping your business running when you are NOT around.
  • The importance of TRUST – how to get over the hurdle of letting go of some responsibilities and trusting another person with your precious business.
  • The 3 BIG questions to ask yourself when you are assessing the need to outsource.
  • Understanding your pain points and how to release them to outsourced talent so you can spend more time doing what lights you up.
  • The importance of asking for help and how you can do it (and not feel guilty).
  • The game-changing act of hiring a VA (Virtual Assistant).
  • The fact that you are NOT as indispensable as you think and why that is perfectly okay.
  • Finding good help and some tips on where to look (hint: old fashion word of mouth rules!)
  • How to write a solid job posting to find the people whose jam it is to do the work that you dread.

Check out these resources to find people to join your team

Ok, so that’s the skinny on knowing when you’re ready to outsource and the Coles Notes on how to start finding good help, my friends. 

I hope you are feeling energized at the idea of bringing in some support and getting the help that’s going to get you out of the weeds and chasing your dreams. 

I want you to remember: You deserve a thriving biz. And you also deserve to not be a slave to time and a mountain of tasks. 

I really can’t say it enough: getting good help is the surest, fastest, way to slaying the mountain of work that stands between you and your goals. Believe me, I know from experience, how outsourcing is truly a life-changing shift that will totally feed your potential. 

Now, I started this episode talking about trust, and I’m going to close on a mindset that’s closely related: control. My darlings, don’t be afraid to loosen your grip, to let a smidge of control go. That too-tight grip is costing you freedom, downtime and growth. You know, all those lovely reasons you got into entrepreneurship in the first place,  right?


Well, you can’t see me but I’m raising my glass (filled with sparkling water, I swear) and toasting to your freedom and possibility. Here’s to freedom and possibility! Cheers and until next week, keep slaying those goals of yours my friend.

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