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Vikram Upadhyaya

Vikram Upadhyaya, Chief Evangelist at GHV Accelerator.

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The Challenge of Being Your Own Boss

Staying motivated is one of the major challenges. Micromanaging everything with no one over your head constantly, can be difficult.

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Photo Credit : glassceiling.com,

Have you just started your own business? Congratulations! You've just signed up for being your own boss before anyone else’s. Your future is in your own hands, and you think you’re almost ready to lead your crew towards growth and, hopefully, prosperity and wealth! You get to set your working hours, you choose your coworkers and you are the controller of your brand. Though entrepreneurship definitely has its upside, it can also be a rude awakening for those who don't have a realistic understanding of the challenges that come with being your own boss.

One huge misconception about being a successful entrepreneur and being your own boss is that it’s glitzy and glamorous. In fact, it’s rather the opposite. It’s extremely difficult, and at times discouraging. Self-employment isn’t for everybody, and the figures on failures of startups and businesses are astounding. But if you have the capability to overcome all the challenges self-employment throws at you, you might have a shot.

Here are what I have found to be the major challenges of being your own boss:

Saying the word “No”: Stereotypically, a boss sets your priorities. He approves the job description and guides you on almost all tasks including managing clients. But now, you set your priorities. While this can mean that you choose your clients and projects, but this can also mean that you have to take hard decisions and take up the unpleasant task of turning down many proposals and ideas. Saying "no" might not feel good, especially when you're just beginning to understand business, but it's an essential step for your venture’s growth.

Setting Your Own Schedule: Dreams like enough sleep and long lunch breaks take a back seat once your business starts to steam up, and being able to choose your own working hours starts to seem like a fantasy. When you thought that you will have no boss, there are 20 clients that set your schedule and you work on their demand. Clients, consumers, contractors, and every other business relationship you have will comprise of deadlines. You will never be able to think of something other than work. 

Marketing Isn’t Easy: Looking at a new product, you never think about all the efforts and work that has gone in, to make it a successful brand. Finished goods can seem so basic in nature that you never appreciate how much labor went into its advertising, not until you are in the same place and you start trying to sell something. Making the society try to purchase something is difficult. This is not something that one can complete in one night. 

Cash Flow: Unsurprisingly, a lot of new entrepreneurs stay awake at night stressing about the money they have moved in and out of their startup. However, by creating a blueprint of your business plans and roadmap of your growth, you can achieve your goals of cash flow management. This exercise can make or break your business. The appropriate financial management tools can also help in saving your time and identifying prospects for growth.

Growth: Managing the growth of your company is the second most challenging task for one-third of the entrepreneurs. However, millennials are losing a lot more sleep over this matter than others. Assessing and managing a growing business takes time and devotion. You need to focus on the small parts of your business one at a time, and when you do expand, make sure your economic management tools are skilled enough to be scaling with you.

Finding motivation: Staying motivated is one of the major challenges. Micromanaging everything with no one over your head constantly, can be difficult. But you have to push through those times and keep yourself busy and keep working. When you can’t find anyone to push you further, you do that yourself.

Reading this might make you feel that it is miserable to be your own boss, but what you have to realize is that your job is your hobby and this is what you planned on doing. Every failure and obstacle you face marks another victory and is a source of pride; this only makes you hungrier for success. It’s the determination in you that can make or break you and can be a key factor in achieving your goals. When you actually think about it, these challenges are just stressors and can be efficiently avoided by proper planning and support. With a fairly strong network and effective tools, these cons can turn into pros. Nonetheless, becoming your own supervisor can be rewarding. When these challenges develop to be too much, think of the fact that every goal in life requires some sacrifice. Else, it wouldn’t be worth it.

Disclaimer: The views expressed in the article above are those of the authors' and do not necessarily represent or reflect the views of this publishing house


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