Getting Started

What you need to know if you want to be your own boss

how-to-be-your-own-boss1
Written by Kate Lopaze

If you’ve ever had a job with a boss, you’ve probably had at least one of these thoughts at some point, especially on frustrating days:

  1. “I could be the boss, and do it better.”
  2. “Why don’t I do that?”

And there are a few different ways to “do that.” One is to rise through the ranks, being a rockstar and getting promoted until get to that place where you’re in charge (though you’ll likely still be accountable to some level of management no matter what). The other way, the true independence route, is to say goodbye to working for others, and go into business for yourself. It’s not the easiest career path, or for everyone, but if this is truly your goal then we can help you figure out how to get started.

Are you truly ready?

Being your own boss sounds great, but if you’re not in a personal space where you’re mature or capable enough (yet) to handle the potentially large demands of running your own business, it’s important to be honest about that up front. Management consultant Steve Tobak recommends starting with an honest assessment of how you are as an employee to see how well you might function in a situation where you’re depending on yourself to get everything done. For example, people who focus on responsibilities over branding and who seek achievements over power will likely be more successful when it comes time to assume responsibility for every aspect of a business. If you’re seeking to become your own boss just to be a boss (and not necessarily to take on additional responsibility), then this career change might not be the right move for you right now.

It comes down to your personal temperament as well. If you do better when given a particular set of goals and benchmarks by someone else, you might struggle a bit when you need to generate those yourself. Or if you struggle with discipline and keeping on task during the workday, there’s a risk that the lack of outside constraints may feed your worst tendencies to procrastinate. Definitely ask yourself questions like:

  • How do I respond to high-pressure situations?
  • Do I get angry or upset easily?
  • How effectively do I organize my to-do list and manage my time?
  • How do I set boundaries in my life between work and personal space?

Creating your own business requires a lot of honesty about your goals and your reality, as well as a lot of good old-fashioned hustle, since you don’t have the framework of an established company to handle things for you. You’re about to be the boss, but you’re also about to be Human Resources, the CFO, the IT department, and the one on the hook for every business decision. If that level of responsibility makes you a little queasy at this point, then maybe it’s best to table the idea for now and revisit in the future. But if you’re still thinking “bring it,” it’s time to start formulating your business plan.

Design a plan.

Your next step should be deciding explicitly what it is you’ll be doing in your entrepreneurial business. Branding is great, but it comes later. The core business has to come first, so a solid plan is essential in making the decision to go rogue. Ask yourself these questions:

  • What kind of service or product are you providing?
  • Who will be your customers?
  • What are you promising to those customers?
  • What sets you apart from potentially similar vendors competing for the same customers?
  • What are your short- and long-term goals for the business?
  • What strategies do you have to achieve those goals?

If you need help coming up with a business plan, there are a number of free and premium services online that can help you craft it, like LivePlan or Microsoft’s Dynamics 365. Every new business is a leap of faith, but you put yourself in a better position with the more information you have about your target audience, your market, and how you plan to develop your business based on the market.

Do a test run.

Before you take the leap, think about doing a “soft launch” by creating your business as a side hustle, or a part-time commitment. This is a way of figuring out if this is the right path for you before you’ve committed fully to the idea of ditching your current path for the new one. Plus, it lets you start building a customer base and getting a real sense of what the market is really like—information that will be invaluable when you get to planning to do this full-time. Take a set amount of time to work on your business part-time, and then re-evaluate whether it makes sense to take it full-time. Sure, you’ll be in for a busy few months while you’re working on both, but consider it an essential research process to test the viability of your plan.

Consider the money.

Before you do anything drastic like quitting your current job, it’s important to do your homework on some baseline financial issues. Finances are an incredibly important consideration here—after all, this is your livelihood. And you’ll be the one writing the paychecks, so there’s not a lot of room for error here if you want to be able to keep your personal finances afloat. Gather your personal financial records and your favorite calculator, because it’s time to answer some brutally honest questions:

  • Are there startup costs associated with your business idea? Will you need to buy specialized equipment or technology? Will you need to buy or rent a workspace? How much money would you need to have up front just to get started?
  • What are the week-to-week operating costs?
  • How long are you able to go without a paycheck, if your business is slow to develop? Do you have enough savings to get you by?
  • Will you need to hire employees or contractors, or will it just be you? If it’s the latter, what can you afford to pay them?

It may be that after your financial analysis, you find you aren’t quite ready to quit your job and go it alone just yet. And that’s okay—it gives you more time to plan, set goals, and lay the groundwork for your business. What’s not quite right for now be much more viable in a year or two.

Decide who’s on your team.

Another essential element is your support network. Your company may be just you at first, and that’s a lot of pressure. What friends or family do you have in place to help provide a balance for that? Do you have people you trust who can listen to you and help you talk through decisions and provide valuable feedback?

You should also start building your network in general, both using online social networks like LinkedIn and joining professional associations in your field. There are also organizations that specifically support small business owners, so you should do a little digging online to see if there are any specific to your field or your state/city/town.

Build your brand.

Self-marketing is going to be one of the best tools you have at your disposal as you get started with a new business. Creating dedicated social media profiles (apart from your personal ones) on Facebook, Twitter, LinkedIn, Instagram, and whatever-platform-comes-next is a no-brainer. And make sure you stay engaged in those accounts, posting new content and updating the world on your achievements, expertise, and services.

You’ll also need a website—ideally, one designed professionally. There are lots of hosting services that also help you build your sleek, functional site. This is not a job for your cousin’s friend’s roommate who wants to test out his design skills. Once you have your own URL and platform, you can use a blog, photo gallery, portfolio, and email to do outreach to potential customers.

Get ready to make the transition.

This is not the time for burning bridges, so you need to think about a careful transition from your current job to your entrepreneurship. This is especially true if your new company will be in the same field. People talk, and other people who make ugly exits will be talked about. No matter how disgruntled you may be in your current gig, it’s important to exit gracefully. That means figuring out a timetable for quitting (potentially more than the standard two weeks) to figure out how to disentangle from your job. You may also want to consider asking your current boss if you can go part-time for a transition period. If that’s not an option, then a traditional exit is fine. You’ll need to give notice, and write a resignation letter. You don’t have to explicitly say what you’re doing next—“pursuing new opportunities” covers it.

During this transition period, you should also see if there’s any fine print in your employment contract about pursuing clients or competitive job opportunities. Some companies have a “non-compete” clause that tries to limit what former employees can do in the same field.

So what do you think? Are you ready to make the transition from employee to boss? Or if not right now, is it something you can see in the near-ish future? We wish you all the best, entrepreneurs, and would love to hear what’s worked for you (and what hasn’t) in pursuit of being your own boss.

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