5 Challenges Every Entrepreneur Will Face and How to Solve Them

By Felicia Guthrie

Taking the leap into entrepreneurship can be both exciting and intimidating, and whether you’ve taken the plunge already or you’re just thinking of it, it’s good to know what you’re getting yourself into. It’s not easy work and you’ll face a lot of challenges along the way. While most of these will be tied directly to your business, they can be a little more personal too.

Here are 5 challenges you’re likely to face as an entrepreneur and how you can deal with them.

CHALLENGE #1: SELF-DOUBT

Self-doubt can pop up anywhere in your journey to being an entrepreneur. You may feel it when you’re thinking of starting a side business, when you’re deciding if you should quit your 9-5, or if you’re starting to doubt your progress. Self-doubt is natural, you’re taking a big step into creating your own business. A good place to start so that you can overcome self-doubt is to build a support system. Find friends, family, mentors, and other entrepreneurs who can help encourage you and lend feedback when you need it.

Sometimes, your overarching goals feel far away and that can lead to self-doubt. Am I doing this right? What do other entrepreneurs have that I don’t? What are they doing that I’m not? It’s easy to compare yourself to others, but that doesn’t mean you should. Create a list of smaller goals and milestones with plans on how to reach them. That way you can celebrate your milestones and goals along the way and when you’re feeling unmotivated or like you’re not progressing, you can review your successes so far.

CHALLENGE #2: FINANCES

Finances can be quite the challenge when starting your own business and many start-ups fail due to financial mismanagement. Finances play a major role in your success, so here are just a couple things you’ll want to keep in mind.

You’ll want to know how much you have when starting out, keep track of expenses and how much is coming in and out each month, and have a contingency plan. Use software programs like Quickbooks or Freshbooks to help keep you on track and make accounting a little bit easier. Search for grants and resources in your community, city, province/state, or country to help get your business off the ground. Having a contingency plan (such as 20% of you budget) in place will help you if anything unexpected comes up along the way, and if the pandemic (and nature: hello hibernating animals) has shown us anything, it’s that having a little extra stored away is a great thing.

CHALLENGE #3: TIME MANAGEMENT

The average small business owner/entrepreneur will wear many hats, you may act as the owner, customer service, photographer, social media manager, sales person, accountant, and more. Sounds like a lot, right? That’s why time management is so important. There are a number of things you can do. Prioritize larger tasks ahead of smaller ones, create a schedule, create to do lists and manage goals (remember, tracking goals is important). There are programs to help you track and manage your time as well, such as Toggl. These programs will help you get a sense of how much time tasks take and will help you chunk out your time so that you can track what you’re doing, when you’re doing it, and how much time you need for the important tasks each week or month. Another important aspect to time management that shouldn’t be overlooked, is setting aside some much needed rest (more on that next), like we said, as an entrepreneur, you’ll wear many hats, and that can be exhausting.

CHALLENGE #4: BURNOUT

Most of us have faced a little burnout before, whether it was in university/college, in our 9-5, or as an entrepreneur. Burnout can also take many forms, for example, you may see a decline in your performance, feel tired and trained, lack motivation, or have a change in appetite. First, it’s important to know more of the signs of burnout so that you can spot them and address them early. So, how can you deal with burnout early? Again, for one, practice scheduling “me time” when you’re taking time management into account. Taking time to rest is one of the most important things we can do for ourselves. Make sure you set time aside to do something you enjoy or simply nothing at all! You can read, go for a walk, paint or get creative, or simply catch up on some extra sleep! It's called a power nap for a reason! Taking time for yourself not only helps you unwind and relieve stress; it can also boost your creativity!

If you’ve already created a schedule, tracked your time, and planned out/tracked your goals, these can also play a role in recovering from burnout. Take a look at how much time you’ve spent working, are you taking on too many large and time-consuming tasks at once that don’t need to be fully fleshed out at once? Is there something you can delegate to someone else (like a partner, employee, or outsource)? Review and rework your schedule and goals so that you aren’t exhausted to the point of burnout. It can take a little bit of time to find the sweet spot, and sometimes you will have to put in a few extra hours, but you’ll get there!

CHALLENGE #5: MARKETING

SongBird Managing Partner, Trevor Shorte, has said it before: “People can’t buy from you if they don’t know you exist,” so of course, marketing is important! There is so much that goes into marketing your business that it can be quite overwhelming for a small business owner/entrepreneur, especially when industries and tech are constantly changing. You have to think of your business plan, your business strategy, messaging, social media strategy, and so much more. We suggest a few things to start, trying listening to marketing podcasts and read blog articles to help get you on the right track. These will offer tips, tricks, fAQs, and insights to give you a foundation to work with.

Want a bit more guidance? You can also book a free 20-minute consultation with us!

Whether you’re in the early stages of entrepreneurship or a little further than that, remember that challenges and obstacles are a natural step in the journey, but they don’t have to be the last step.

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