4 Lessons You Should Learn Before Launching a Second Business

Kayleigh Alexandra

6 min. read

Updated October 29, 2023

Download Now: Free 1-Page Business Plan Template

In most ways, the easiest way to approach a career is to follow the norm and pass the buck to an employer. Let them find work for you and pass it along: you can live a simple life, just getting through your assigned daily workload and not needing to think about anything else. Minimal stress, minimal responsibility, and minimal opportunity for failure. There’s a lot to like.

But maybe you can’t accept having your destiny shaped for you. Maybe you need to bet on yourself: your ability, passion, and drive. Some people are like that, and we need those people. Entrepreneurs take the risks that ultimately give rise to the businesses that are able to keep so many people gainfully employed. They thrive on facing and overcoming challenges.

And while there are many cases in which professionals come up with isolated business ideas to pursue, it’s also extremely common for entrepreneurs to want more after they’ve successfully established their first businesses. Pursuing more can be a great thing, but it can also prove disastrous. It’s all about how it’s handled — and in this post, we’re going to run through four lessons that you need to learn before you move forward with launching a second business.

1. Comprehensive planning is key to mitigating risk

When you’re trying to get your first business up and running, you might just be able to cope with having no optimized plan if you’re tremendously lucky — but that luck won’t last forever. Double down on it and you’ll be setting yourself up for failure. The smart thing to do in that situation is to be grateful for your previous fortune and do what you can to rely on fortune less in the future.

  • What do you want your second business to be?
  • What type of business model will you use?
  • What boxes do you need to tick?
  • What research must you do?
  • How will it complement your existing business?
  • Is there any risk of overlap or competition?

There are plenty of resources out there to guide you through what you need to do. If you’re looking for a template that can work for any small business, the Bplans template is an obvious choice (not just because of where we are). If you’re concentrating specifically on eCommerce, 

Learn With Shopify has a great video guide (see above) with some useful tips to follow.

The more time you put into planning now, the less risky your second business endeavor will be — and since the fate of your second business will have knock-on effects on your first business (potentially starving it of resources and/or attention, or sullying your professional reputation), this is necessary to protect everything you’ve been working for.

2. Outsourcing is essential for scaling and expansion

Solopreneurs have become massively more common in recent years, empowered by the ease of working from home, the development of powerful and intuitive productivity tools, and the growth of straightforward automation. There are plenty of small businesses that can be successfully run without teams. Dropshipping is a typical example, but there are also consultancies, graphic design services, and even software development services.

Despite the big drawbacks, there’s a lot to be said for doing everything yourself. You get to keep all the profits, save a lot of recruitment time and effort, focus entirely on what you’re doing, and avoid the potential headache of dealing with HR. When you reach the point of starting a second business, though, it’s foolhardy to make a serious attempt to remain a solopreneur.

This is why outsourcing is essential. You don’t need to bring in full-time employees, but you do need to identify the tasks that you’re not best suited to handling and find some reliable freelancers to lighten your workload. This will immensely improve the quality of the work done for those tasks, and it will free you up to concentrate on your role as a manager and figurehead (more on this next).

Brought to you by

LivePlan Logo

Create a professional business plan

Using AI and step-by-step instructions

Create Your Plan

Secure funding

Validate ideas

Build a strategy

3. Burnout is a danger to every business you run

Professional burnout isn’t something to be taken lightly. It isn’t about feeling a little tired sometimes and needing to take a day or two to compose yourself. It’s about working so hard for so long (and building up so much stress) that you simply lose the ability and inclination to endure your regular workload. It isn’t typically permanent, but it is entirely possible to burn out so extensively that you can never build up the will and desire to go back.

Outsourcing all but your core tasks is a huge component in avoiding burnout, but not the only component. You also need to accept your limitations. It’s hard to see that you’re not invulnerable when you’re single-handedly keeping everything running in your first business, but that feeling won’t last — following the tips in the video below will help if you’re in a difficult position and overworking yourself:

Now, you might think that you won’t burn out because you love what you do. Well, while it’s true that we can endure extremely difficult conditions if we’re driven by passion, this can’t keep you going in perpetuity. Sooner or later there’ll be a disconnect between your character and your professional circumstances (this is explored more in the above video from psychiatrist Dr. Tracey Marks), and you’ll struggle to cope.

Burnout induced by your second business will affect everything you do, and it’ll be even worse in the event that you do have in-house employees. You’re supposed to set the standard for everyone else. How will it look when you’ve expended all your energy and stepped away from your role for an indefinite period of time? Pace yourself, find time to relax, and set reasonable goals that won’t push you to work ridiculous hours. It’ll be so much better for you in the long run.

4. There’s no guarantee that it won’t completely fail

Think of a first-time gambler heading into a casino to play roulette. Now imagine the following two possibilities: they win big on their first spin, or they lose and get nothing. In the former scenario, they instantly get the feeling that they’re somehow destined for success, and bet everything they have on the next spin. It doesn’t go their way, and they leave dejected.

In the latter scenario, that initial loss reminds them that it’s a game based on chance. If they keep playing, they do so knowing the nature of the risk they’re taking, and any subsequent loss doesn’t hurt as much. In addition, if they win more than they started with, they’re much more likely to quit while they’re ahead instead of sticking around to chase even greater amounts.
This is relevant in the context of launching a second business because it’s entirely possible (though not hugely common) for an entrepreneur’s first business attempt to be a major success. And when that happens, it can lead them to believe that they are indeed destined for greatness: an attitude that can lead them to be flippant in the organization of their second business.

Approach a second business like it’s your first

Here’s the truth: no matter what you’ve done before, what you know, what connections you’ve made, or how much you’ve achieved, your future success is not guaranteed. Instead of putting all your savings and profits towards your second business, treat it accordingly: set aside some money for a reasonable budget, prove that it can work, then invest in it more heavily.

Once you’ve done a great job with one business, starting a second business might be the natural move — but don’t leap into it before you’ve learned the lessons we’ve been through in this post. Ensure that you’re fully prepared, then take the leap. It will help you avoid running into a disaster.

LivePlan Logo

Clarify your ideas and understand how to start your business with LivePlan

Create Your Business Plan
Content Author: Kayleigh Alexandra

Kayleigh Alexandra

Kayleigh Alexandra is a writer for Micro Startups, your online destination for everything startup. She's passionate about hard-working solopreneurs and SMEs making waves in the business world.