Tagged: entrepreneur

5 Things to NOT DO and 5 Things TO DO When Starting a New Venture

As I begin my new business * venture tomorrow, I reflect on where I was a year ago.

*(Details and Discounts available here)*

A year ago, I had just quit my full time job at a Fortune 500 company in Chicago. Very shortly after I had started working for the company, I acquired this irrepressible desire to start something new, to be my own boss, and to be a part of something that was important and bigger than I was! This desire only grew stronger with each day and never wavered.

So, instead of continuously complaining or hunkering down and wishing for the best at that point in my life, I decided to start something new. A year later, I am still learning and growing, and it is magnificent. This list here is a little bit about what I have learned.

Below are 5 things I would tell my former self NOT to do in the beginning stages of venturing into uncharted territory, and 5 things I would tell myself to be sure TO DO. Hindsight is always 20/20, right?  Feel free to take what you think will work for you and share with others.

When Starting Something New


1- Do not try something new to seek happiness alone. Obviously we all want to be happy in life, and we deserve it! However, when you are starting a new venture, you can’t do it only because you think it will make you happy.

A while back, I read an article by Adam Grant (professor at The Wharton School, organizational psychologist, and author of Give and Take); it was called “Does Trying to be Happy Make Us Unhappy”.  This article changed my perspective on a lot of things. A portion of the article outlines the importance of finding work and experiences in which we achieve a state of flow; where we are so involved in what we are doing that we lose track of time and never stop to ask ourselves if we are happy. Once we stop and ask ourselves if we are happy, we shift from an ‘experiencing mode’ (a.k.a. the ‘flow state’ which is the ‘optimal emotional experience’) to a ‘mode of evaluation’; “…a wealth of evidence consistently shows that self-focused attention [being in a ‘mode of evaluation’] undermines happiness and causes depression.”

My take on this unforgettable article is this: If you are too busy searching for happiness, you will be too busy thinking and hoping and dreaming to actually experience it. Your dream of happiness will remain untouchable if it is not grounded in the work that you produce; the work that consumes you and that you genuinely enjoy doing, especially when things become challenging. And in order to experience happiness, this work must be focused on others or something that does not provoke you to self-evaluate and ask how it is affecting your happiness levels.

The work itself is what allows you to experience a state of flow—work you enjoy doing. And it’s going to take a lot of work in the beginning. You should start something because it keeps you intrigued, motivated, and allows you to grow professionally and personally; it allows you to continually learn and challenge yourself, and allows you to contribute to something outside of yourself.


2- Do not underestimate yourself and overestimate risks. Every single one of us has something to offer, and something unique about us that will allow for us to shine. Let your unique light shine, and let it inspire others. One of my all-time favorite quotes- “Everybody is a genius. But if you judge a fish by its ability to climb a tree, it will live its entire life believing that it is stupid.” So, embrace your inner genius and what makes you unique and don’t get lost underestimating yourself by measuring your abilities according to others’ standards, especially if they do not apply to you and your work. Know your value and don’t be afraid of bringing it to the table when it is time to do so.

More importantly, don’t overestimate the risks you are taking when starting your new venture. Ask yourself if they really are as catastrophic as you think. Margie Warrell outlines this well in, “Do You Overestimate Risk And Underestimate Yourself?”:

“…consider where you need to lean toward risk rather than away from it.

Even if things don’t go exactly to plan, you’ll still be better off. Every time

you take a risk, you improve your ability to discern risk, your competence to

manage it,  and your courage to take them more often.

You are braver than you think and can do more than you know.”


3- Do not think you have to be perfect. We all appreciate authenticity and someone who shows a little vulnerability. We all have our insecurities; be honest about them with yourself and don’t think that you need to come off as the expert of absolutely everything, or that you need to overcompensate for your shortcomings. We all have shortcomings. We all have bad days.

Remember, starting your venture will be a learning and growing process. You have to remain open to learning and challenging yourself, every day. And if there is a task you’re not that great at, then outsource. Build a network of people that love to do the things you aren’t so great at or the things you don’t particularly like doing, and they will rely on you to fill in the gaps in their businesses or ventures as well.

Clients and cohorts appreciate it when you understand them and can communicate on their level… when you show a little humanity—“…THE reason why I have a successful business. I don’t try to be perfect anymore. In fact, I love when clients can see me in imperfect moments. These exact moments show them that I too am human” (source). And those who follow you, work for you, and support you, don’t want to be set to unrealistic standards either- “Many driven executives struggle to accept that flaws and mistakes are part of being human. And when you act as if you are, or should be, perfect, you eventually expect it of others as well. The followers on whom those unfair standards are imposed typically revolt and withdraw their support.” (Harvard Business Review, source).


4- Do not think that you need to have all the answers. Refer back to #1 above. If you are truly seeking a path that is intriguing and important to you, then nurture it and allow it to organically grow. Also refer to #3 above. You don’t have to be perfect or strive for perfection. Don’t be afraid of failure and don’t be afraid to start over again, especially when something is not working.

And while it is perfectly fine to research business and marketing ideas, take online classes, and go to multiple networking events, don’t think you need all the answers right away. Over time, once you start producing and sharing your work, you will get the hang of what works, what doesn’t work, as well as your opportunities for growth. Have a plan, but don’t plan for too long.  For more ideas and inspiration on how to show your work before you think you’re ready, read Show Your Work!  by Austin Kleon; seriously, read this book.


5- Do not keep negative people around. If someone brings your positive attitude down on a consistent basis, then it can take a toll on your ambitions and resilience… which you most certainly need a lot of when starting a new venture. Advice: give them the boot. Consciousness is contagious. And if someone is consistently breeding negative thoughts and emotions around you, you will feed into this without realizing it, and it will affect the quality of your work and relationships.

Always be on the watch for haters. While “we should always look for ways in which critics can help us grow. We should always humble ourselves and listen to voices of disagreement.But (and this is important) if someone only wants to criticize and isn’t willing to engage in dialogue, that person is not a critic. They’re a hater” (source). It’s always best to ignore the haters and get on with what you do best, your work.


And now,

When Starting Something New


1- Do- Keep a journal and reflect often. Take 10 to 15 minutes every work day to reflect on what you have accomplished for the day, good ideas that came to your mind, good advice you received, what needs improvement, and what you want to accomplish the next day. This is a great way to stay motivated and organized.

If all you are ever doing is looking at to-do lists, without reflecting on what you have already accomplished, you will get overwhelmed and loose site of the big picture. Your motivation will falter. Reflecting on accomplishments and aspirations will help you maintain your motivation. And if you never set tasks to do the following day, outlining where you left off the previous day, you will start the day without a clear agenda. You’ll probably revert to answering emails or posting on social media sites first thing when you start your day and will lose a lot of time that you could be using to produce your work.


For more tips on how to start a journal and its additional benefits: source 1.


2- Do- Test things out to see what works. We are very lucky to live in a world nowadays where data about our target market is so easily accessible and discernible. If you aren’t sure of who your target market is, then don’t be afraid to test things out. Post a few Facebook ads geared toward different groups. Track the results of the responses and activity you receive, and see what works. Use the market insights and data provided by social media sites and your website hosting or blog hosting services. Remember #4 from the above “Do Not” list—“Do not think you need to have all the answers” when you start. Let the data help guide you.

The most important thing to remember is that you want LIVE PEOPLE to be engaged with your content. While content and information that is search engine optimized is important, it will only get the goals you have for your new venture so far. Until you are able to determine who wants to engage with your content (not a robot), test a few different avenues and types of content in order to see what people want to engage with, at what time, from what avenue, as well as other interests they might have.

Here is a list of 10 Questions to Ask when deciphering your target market.



3- Do- Exercise, sleep, and eat healthy food. Make sure that you take care of yourself first. If you aren’t taking care of yourself, you won’t be able to take care of business.


It’s simple. If your body isn’t getting the nutrients it needs and the sleep it requires, it will not run efficiently. And if your body doesn’t get adequate exercise, it won’t be conditioned to handle the day-to-day stresses that come up. Check out Time’s list of Deskercises you can do while you work.


And most importantly, make sure that you take breaks! When starting a new venture, it’s easy to want to work constantly, especially if you are a solopreneur. However, “A growing body of evidence shows that taking regular breaks from mental tasks improves productivity and creativity — and that skipping breaks can lead to stress and exhaustion”(source). You can even complete a few deskercises during one of your breaks if you must multitask.



4- Do- Know who you are and follow advice that makes sense for you as a person and the path that you are on. If you like to make jokes, then make them (yes, even in business) because you are going to find the folks that want to work with you because of that unique trait you have. Be your authentic self. People can tell when you are faking it and they won’t want to engage with what you’re doing. Would you? Remember #3 from the “Do Not” list above—“Do not think that you have to be perfect.” If you are extra analytical, embrace that, it means your work will be extra thorough and reliable. And if you are getting advice that doesn’t seem right to you, even if it is from a “thought leader”, then scrap it. Thank them kindly and move on because you need to grow with your new venture as your unique self.

If you know what makes you tick and are willing to grow and learn with your new venture, then you already have a lot of the ingredients for success. Here’s an article about why you should try to know yourself before starting a new venture.



5- Do- Have a strong and positive support network.—I personally don’t care what industry you’re from; if you are inspiring, positive, or bring a value to the table that I don’t offer, then I want you in my network. There is so much to learn and you never know from whom or where you will get your motivation from next. And we are incredibly lucky how easy technology makes it for us to connect with one another. Find your top two favorite social media sites and start connecting with people who share your interests, concerns, questions, hobbies, etc. Call up your old cohorts, colleagues, cousins, neighbors, pastor, bosses, second grade teacher, car salesman… the list goes on and on. There is always something to learn from someone else.

Here are some ideas for How to Build a Powerful Professional Network . And if you aren’t sure where or how to meet people (especially if you are a solopreneur), hop on Meetup for local events in your area.


These are some items that I like to keep in mind when starting a new venture. What would you tell yourself to do and not to do when starting a new venture? Be sure to leave your answers in the comments below!