Being your own boss sounds like the dream. You get to set your own hours, choose the kind of work you want to do, and work when and where you want to. But entrepreneurship isn’t all roses, or your uncle Jimbob would totally be doing it. If you’ve been thinking about trading in your cushy W2 life for an exciting LLC, make sure you go in with eyes wide open – and a working knowledge of the pros and cons. After 4 years of doing this, I’m ready to share some home-grown wisdom with you.

Loneliness and workload extremes: Entrepreneurship cons

Let’s start with the cons. Because let’s face it: entrepreneurship isn’t for the faint of heart. And if the below is enough to scare you off, then it’s for the best, trust me. Here are some of the challenges you’ll face if you decide to go out on your own. 

1. Inconsistency. If you thrive on routine, this might not be the gig for you. Solopreneur life comes with a ton of inconsistency built-in. This is especially true if you’re selling services (or one-off products). Clients might need your services for a month or half a day. They might be on your books for a year, and then disappear. Ebbs and flows are normal, so have a buffer for dealing with scheduling gaps – and make sure you’re not resting on your laurels if things are going well. Always be hunting down that next big thing. You can’t control the market, but you can control you.

2. Working in a vacuum. Social butterflies need not apply! This lifestyle might look cool when it’s on the front cover of Fortune magazine, but entrepreneur life can often mean working long hours all on your lonesome. Sure, office life is full of annoying meetings and chitchat, but it also provides opportunities to bounce off people, have organic conversations, and collaborate. If you thrive by being around people, set up your new working environment so that it puts you in the action – rent a desk in a coworking space, meet clients at coffee shops, or join networking groups and events. Lean on like-minded people, not friends and fam.

3. Lack of benefits. Those payslips at your current job track paid leave, sick leave, retirement and healthcare. When you go out on your own, you’re in charge of all that stuff – plus expenses like accounting and legal. Make sure you include the “cost” of these things in your rate. Protip: set expectations and draw lines with clients and your team members when it comes to your availability. If you’re *always* available, you’re training others that they can contact you whenever and wherever, which makes it even harder to take time off!

4. Imposter syndrome. At your last job you probably jumped through interview hoops and earned your promotions by checking off a bunch of seniority and achievement metrics. Plus you’ve got the backing of your team and your company. But as an entrepreneur… it’s just you, babe. Gulp. Sometimes you’ll be flying high, and other times you’ll be feeling like a big ol’ fraud. Get in the habit of talking yourself up, surround yourself with people who will cheer you on, and give yourself opportunities to prove you know your stuff – because you do! Knowing you’re delivering value will help you remember that you hung out your shingle because you’re a pro.


Yoga pants and no commute: Entrepreneurship Pros

Still feeling like this entrepreneurship thing might be for you? Good job! Because it’s all upside from here. Here are some of the perks of being GoGetter, LLC.

1. Prioritizing what matters. Entrepreneurship lets you build your career around other priorities like family, kids, other passions, or travel. Instead of squeezing those things in around your work, you can shape work around them instead. But make sure that you do – when it’s just you running things, it’s easy to end up working long hours because you don’t want to let people down. Be self-aware and make adjustments without sacrificing your core priorities.

2. Enjoying life stuff! Need to go to the dentist, work out, get the dog groomed, or swing by the post office? Living la vida entrepreneur-ca means you can flex your day around whatever else you have going on. Shopping during the week instead of on the weekend, or working at night so you can attend a conference makes life run more smoothly – and enjoyably. 

3. Working from anywhere. Have laptop, will travel. When you’re an entrepreneur, you can work where and how you want. From your home office, between sets at the gym, a local coffee shop, or a rotating selection of your favorite coworking spaces. If you need to dial up your creativity or find some inspiration, mix things up by setting up shop in the park, by the beach, or in a totally different city. Not being trapped in a fishbowl cubicle is a major win.  

4. Bye-bye, commute! Sure, you can commute into an office if you really want. But you don’t have to do it in peak hour or in the direction everyone else is going. Skip the tolls, circling around looking for parking, and those 2022 gas prices by walking the ten steps from your bedroom to your home office instead. 

5. Making lots of money. A W2 salary is great, but there’s generally an upper limit on your earnings. As an entrepreneur, the sky’s the limit. You can work ten hours a week if you want (and bill high enough), or build a team to deliver serious value – and profits. When you work for yourself, you can set your salary, your hourly rates, your payment terms, and your own 401(K) match.  

Ready to take the plunge (or not)? Already making a killing living that solopreneur life? Let’s connect on LinkedIn – and lift each other up!