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  • Writer's pictureDennis

Why Is Entrepreneurship Considered a Lonely Journey?


Why Is Entrepreneurship Considered a Lonely Journey?
Why Is Entrepreneurship Considered a Lonely Journey?

There are lots of reasons entrepreneurship can be a lonely journey and several business owners will encounter a mixture of them. Some are avoidable or preventable, others less so. Most can be managed.


But all entrepreneurs will feel lonely at numerous stages of their journey, perhaps constantly, if they don’t have a great support network and good emotional hygiene.

Here are three common feelings I’ve heard from other entrepreneurs that I’ve encountered to varying degrees myself:


1. Disconnect with Family and Friends


Many family members and friends won’t understand what you’re doing or be able to relate to your problems. Likewise, you may struggle to relate to theirs. You’ll get pushback on what you’re doing, like “get a real job,” and experience envy from some if you’re successful.

If you become super successful in an obvious way, it could become tough to work out who your real friends are.


People make lots of assumptions about what it’s like to be an entrepreneur, and many of those are false. As entrepreneurs, we often struggle to see why people would choose to live a different way. It’s important to keep a check on this or you’ll end up very lonely indeed.

Surround yourself with people who share similar values with you, but also those who are very different, so you stay grounded. Make an extra effort to listen and understand others. Don’t continually preach about why everyone should go out and start a business or something similar.


Try your hardest to see people’s perspective even when they’re ranting about their stressful boss who undervalues them, even if they’re trying to convince you to chuck it all in and get a 9-5 at a bank, or tell you about their great business idea that they want to turn into reality “one day” (but can’t now because of X, Y or Z rationalization). Learn how to support, not just advise people. They’re two very different things.


2. In the End, It’s on You and Only You


When it’s just you, or perhaps you and a co-founder, you won’t feel the weight much. But you don’t have to grow much at all before you begin to realize that people are relying on your capacity to make the best decision every day and that no one can make many of the biggest decisions but you.

Your investors, advisors, board, employees and executive team can all give you their take but in the end, you’re the person who has the final say. So you have to hold yourself accountable for everything your company does. That’s your job.


As your business grows, you’ll increasingly see that no one else can do the same thing you do no matter how much you try to share, document or articulate what’s in your head. Businesses are complex and in a constant state of flux.

Building friendships with fellow entrepreneurs and developing strong co-founder relationships help here.


But it doesn’t get rid of the fact that people have put a lot of trust in you. You have to get used to this and accept that you’re not perfect. Also, accept that you’ll make imperfect decisions because you’re constantly making decisions with imperfect information. Some of these imperfect (or straight-up bad) decisions will have major consequences at some stage.


3. You Have to Make Time for Everything


You don’t have to progress far through your journey to realize there’s always more you can do, or there’s always another person, task or project that wants your time in some capacity: extra work you could do on the weekend, dinner meetings you can take, events you can attend, customers you can visit, or entrepreneurs who want advice. The demand for your time never stops growing.


That means you have to make time for your friends and family, and choose socializing, hobbies or “chill out time” over work. You pretty much have to schedule it to make sure it happens. That’s not always easy as your time increases in value, monetarily speaking. But if you don’t do this, you’ll soon feel burnt out and truly alone when you need others the most.


It’s All about Balance


The best thing an entrepreneur can do is accept that their journey will often be lonely. Then find ways to stay connected with people, have other hobbies or interests, make time for people, and develop a system of values which you won’t compromise—something that is true to you.


But if you don’t do that, the consequences are grave.  You’ll probably find yourself lying alone on your death bed one day, saying “I wish I hadn’t worked so hard,” “I wish I had stayed in touch with my friends,” or “I wish I had let myself be happier,” to the poor nurse who is upping your morphine dose again.


Wantate Dennis.

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