Challenges of Entrepreneurs

I originally posted the question below in the LinkedIn Group – Entrepreneur’s Network. However, I wanted to share the conversation outside the group. It’s an interesting discussion on the challenges Entrepreneurs are currently facing. Those challenges span both their personal and professional lives. Many people believe we can separate our professional and personal lives. In theory, this concept sounds appropriate. However, let’s be honest for a moment … when we face difficult challenges in our professional lives, it will impact our personal lives. If we positively improve our personal lives, it will enhance our professional lives. Everything is interrelated.

As an Executive Coach, I focus on building dynamic leaders and solving business challenges by increasing overall happiness and well-being. You have no idea how many times I’m hired by a client to work on a “business” challenge, but through the coaching process, we discover the correct answer comes through removing a filter or mental road-block. As leaders, we view our business circumstances through filters that based on our experiences, values, assumptions, etc. Those filters either limit or expand our ability to access potential solutions.

Often, we already know how to solve their business challenge (The What), we are just having trouble accessing the solution. Once we remove our filters or mental roadblocks (The Who), there’s an almost instantaneous shift in focus and energy … answers begin to flow and the energy to execute increases.

As you read through the discussion below, can you spot the interaction between “The What” and “The Who”? Can you see instances where our personal and professional lives are impacting each other? 


Quick Concept:

The What: Systems, Process, Structure, Strategy, Tactics, Plans, etc.

The Who: Our filters, assumptions, limiting beliefs, mental roadblocks, etc.


The Question:

“Over the last few weeks, I've been watching my LinkedIn groups. There's a lot of people posting articles (I do too), but not engaging. I'd like to change this if possible. I'd enjoy hearing about YOU, your business, and/or what you are working on? What are your challenges? What are you struggling with personally or professionally? Anyone open to that?”

The Discussion (copy/paste):

Andrea Richardson – Founder @ ICPromise

Sure! For me, it is finding the time to do more and still have time to stop and smell the roses.

Stewart’s Response: Andrea, I obviously don't know your circumstances. However, how much time is enough time to stop and smell the roses? 5 minutes? 1-hour? 1-day? It's a personal question. You are the only one that knows the answer best suited for you. But, it's extremely important to our well-being to have those moments. Have you considered always keeping a fresh set of roses near you? Maybe always having roses nearby can be your mental reminder to "stop and smell the roses." Maybe it will remind you to take 5 minutes, be present and celebrate the small wins too. Even if that small win was finding time to enjoy a cup of coffee in the morning. 

Heck, maybe stopping for 10 seconds to actually smell the roses could help. :)


Eric Block – Network Marketing Trainer

I hate to say it, but is it ego/false pride that keeps people from opening up and engaging in true dialogue on any given topic, less they expose any kind of weakness. I mean for me to tell you I am a struggling network marketing distributor, I worry that will show me as being an unsuccessful person, and I won't attract anything useful for my life here, and pity is not useful lol.

Stewart’s Response: Eric, thank you so much for your comment. Very bold and brave! I’ve experienced that in this world, there are so many people that are ready and willing to help others. People have amazing hearts. Many of those people have struggled as well and all they want to do is help others going through the same challenges. I’d be willing to bet if you reached out to the world, presented your specific challenges, and asked for advice … the advice will come (for free). Think about this discussion group. Look at all the people presenting their challenges. I’m doing my best to give them my thoughts and advice. Have you considered finding a group or platform specific to your niche, energetically presenting your challenges, and seeing what kind of advice comes back? Maybe find a few groups on here and FB. Posting a question or series of questions on Quora comes to mind as well.

Last, you mentioned the term “attract.” Remember, energy attracts like energy. Consider reframing how you are thinking about your challenges. Instead of “worrying” about showing yourself as “unsuccessful,” be PASSIONATE about the fact that you can “learn and grow from others!” The energy you present will attract the same energy. Worry attracts worry. Passion attracts passion. Do you want to appeal to people that “worry” too? Or, do you want to appeal to people that are excited and passionate about Network Marketing?  


Kevin Roney – Owner (Acting CEO) – Energy by Design

Struggles....great topic.  Personally, I have had a number of projects that failed to execute well recently.  So, I've temporarily shrunk the funnel and active projects to try to regain strong execution before taking on a number of new requests...but, you know...that has only really resulted in a lot of lost revenue.  While there are times when it's appropriate to say no to business...I've learned shrinking the portfolio is not the right approach.  Raise the bar fast, solve the issues, and take on every bit of business you are awarded.

Stewart’s Response: Kevin Roney that is super tough. For me, some days/weeks/months I am so busy that I barely have time for anything else. An amazing shiny object pops up. Oh, that is awesome. Yes, I want to do that! I start thinking ... I need to hire somebody else to help. I don't. I push through, hit the deadlines, and over-deliver. Then, everything slows down again. "Nah, I got this." No need to hire. Then, the cycle happens again and again and again. I'm trying to break that cycle. Do you or anyone else have recommendations?

Kevin’s Response: Stewart, great comment (#ShinyObjects).  I see this happening so much to myself and others in my circle.  So many comments...but I should not type a book.  Bottom line, create a vision, structure a strategy around this, with limits and milestones.  Anything that supports, take on.  Anything that doesn't, don't.  Set a threshold when something becomes sustainable (to hire, grow), otherwise, gut it out and absorb with the current team.  I should write a blog...so many thoughts and advice!   


Joe Hancock – Marketing Consultant – Virtual Financial Group

I'm all for that. I do try to engage with people by asking questions when I post stuff, but all I get are likes. Kinda frustrating at times. I confess though, I'm guilty of not posting in the groups as much as I should. I will do better.

Stewart’s Response: Joe Hancock thank you for your comment! I agree it is frustrating. We have all done it too. All we can do is focus on and improve what we can control ... our actions. Keep up the great work!


Ashley Renia - Owner – Blue Sky Bookkeeping

Hi! I am starting a bookkeeping business from nothing and my struggles have been trying to get my business noticed, learning how to market it, and not forgetting how to do bookkeeping while I learn to be a marketer! I haven’t had much engagement either, so that would be so helpful. I don’t have much of a budget for advertising so using platforms like LinkedIn are important for me. I am trying to learn how to make posts that will get engagement, but so far no luck! I do read through what others are sharing and share and like when I enjoy what they shared. I try to do my part!

Stewart’s Response: Ashley Reina congrats on starting your new business!!! It's an amazing adventure. Each day you'll get better and better at marketing your business. Take it one day at a time. Have you considered informational interviews with prospective clients? Anyone you meet and/or people on LinkedIn ... if they're a potential client, you could always ask to do an informational interview, NOT a sales pitch. You are simply trying to understand the challenges of SME business owners, what they look for in an Independent Bookkeeper, how they learn/find contractors to help them, etc? I'm sure you could put together 5-10 questions to ask someone over 15-30 minutes. 1) You learn more about your potential customers and can translate that into better marketing. 2) They become indirectly aware of your services. Caution: If you tell someone you are doing an informational interview ... DON'T sell them your services (unless they ask). Conduct the interview and learn from it. Just something to consider.

Ashley’s Response: Stewart Swayze I have tried to do that! I have put together a few questions about what they need and the problems they have. I haven’t gotten any responses yet, though. I am going to keep trying! Thank you for the kind words and the free advice!


David Arandle - Owner, Art Director – Animation for Business

I'm pretty new to LinkedIn in the sense that I've had a profile here for years but only in the last few months have taken the time to really understand the platform by taking a couple of courses.

Both courses said groups are the real benefit of LinkedIn for finding leads and making connections but the majority of groups I've joined all I see is an endless stream of reposted articles.

Articles are great but it's a bit like running around a network event with a magazine and saying 'Have you read this article?' and then waiting around to see if the person has interest in it. You probably wouldn't do that.

I feel the better approach is to take an interest in people, start actual discussions (like this one), and just get to know who's in the room with you and what they're about. Don't pitch but, you know, let people know what you do naturally through discussion... or just be interesting enough that people are motivated to look at your profile... that's one approach any way.

Stewart’s Response: David, thank you. Amazing insight. Be present. Actively listen. Build relationships. I like it!


Kaur Lass – Managing Director - Conscious Initiative PLC & wellnessorbit.com; Planning Expert & CEO at Head OÜ

Hi! It seems that when LinkedIN restricted the length of comments some years ago the platform took more superficial approach. It used to be deeper discussions and true exchange of know-how. I loved those old long discussions! Now it has been for several years more superficial.

I see that superficiality is a major problem all over the workplaces. I and my team once wrote the story about this: https://www.wellnessorbit.com/newsletters/the-cost-of-being-superficial/id/14

This very superficial approach also causes lack of engagement not only here, but also with the work that people do. So, the lack of employee engagement and also mental health problems are taking more and more epidemic proportions!

Stewart’s Response: Kaur Lass thank you for your comment and insights! Very interesting. What would you recommend we can do to solve this?

Kaur’s Response: Stewart Swayze Well there is listening and there is listening with full awareness: http://www.hrmagazine.co.uk/article-details/effective-listening-by-using-awareness - we should try to post less and more meaningful things (do not post, if your post is not really giving anything besides superficial tips and tricks) and then listen what people have to say! How does this sound?


Steven B – President/Founder - Refined Strategy LLC

I like Ashley Reina, I am trying to learn how to market my new business. In January I started a business consultancy firm. Which is fancy for, "I share my knowledge and skills with anyone for a price." When I first opened the doors I thought that I would be able to find clients pretty quickly. After all I could clearly see those who needed my services. But I quickly learned that creating a strong consistent message which communicates the value of your services is A LOT harder. I also started my business with under $1K. Thus far I've had only one sale. I have not leveraged the groups here yet. I hope this is the start of a real valuable exchange of ideas and strategies.

Stewart’s Response: Steven B. I know exactly what you are going through! I've been an independent strategy consultant for several years now. I've grown my business through a multi-channel approach. Social Media Marketing, Partnerships, Referrals, Networking, etc. I'm really focusing on partnerships and referrals now. As I look back, I'd say 90% of my closed deals came from those two sources. You should also find ways to generate alternative revenue streams. Revenue/Cash flow will be variable. Look into ways in which you can continue to use your skill sets, but not be dependent on a "project." Example, digital courses, community workshops, speaking, etc. 


Heather Becker – Online Fitness Coach

Good morning! I’m an online fitness coach with Beachbody. My biggest challenge is time management with family and work!

Stewart’s Response: Heather Becker that you so much for your comment. Time management and work/life balance is a really tough one! I've been trying to do a better job at prioritizing my time and delegating to virtual assistants/contractors. I break my time down into 3 categories: $1000/$100/$10. Anything that's a $10 task, I immediately delegate. $100, might delegate/might do myself. The $1000 tasks are my highest priorities. One, I can focus on the highest value tasks. Two, I free up time for other personal activities. Have you done anything like this?


Dora Herrera – Owner - Yuca’s Restaurants

Stewart, thanks for getting the ball rolling.

Our current challenges are:

1. Translating being liked into sales.

2. Having people understand that our quality product requires a price consistent with that quality (no .99 tacos)

3. Increasing awareness in a younger customer base since we've been in business 43 years.

Stewart’s Response: Dora Herrera thank you for being so transparent about your challenges. Obviously, I have only the information you've provided.  It sounds like you are targeting the "younger customer base." Is this the group that is liking, not understanding quality, and hard to increase awareness with? If so, have you conducted VoC to determine what they value from the products (tacos) that you sell? Where they like to receive information and awareness of your kinds of products? My only thoughts are that maybe you could target a different group that values the quality? Then, use that group to bring in the younger generation. Or, if your most strategic customers don't value quality, you might have to consider adjusting to the market???? I've always learned that the best way to understand what your customers want ... is to ask them. Of course, everyone will say, lower price, but you might be able to find out more than just pricing. You have 43 years of experience, I have no doubt you'll figure this out


Jack DiMatteo, CPA – President – Executive Overdrive LLC

 Thanks for opening the discussion Stewart. Third time this week I’ve seen a post about the lack of engagement. Seasonality seems to be partly to blame (or maybe just a convenient cop out). I see these as the main reasons people engage on LI:

 1) Job seeking

2) Recruiting candidates

3) Building a list of valued contacts

4) Exchanging ideas with like minded professionals

5) Marketing or selling their services or products

 Over the years 1&2 have begun dominating the site. 3 always makes sense. 4 has really fallen off because the members I speak with don’t see a return on the effort it takes to stay engaged. Usually 4 is being done in the hopes of assisting with 5. People are horrified when they get “pitched” on LI.

 My take is that an ever increasing number of users aren’t seeing a great enough benefit for staying engaged.

 Stewart’s Response: Jack DiMatteo, CPA thank you for your insights. Do you have any thoughts on how to correct the challenges of 4 & 5? Your comment on people being horrified when they are pitched on LI, do you believe it's because nobody understands or has received training on "social selling?" tactics?


 Michael Jordan, MBA, PMP – Founder – AnthroDesk

 I've been trying to engage more recently myself, but if others are like me, it takes a little while to get used to opening up on a platform like this.  One challenge I experience is balancing my business and personal life.

 Delegation has been a big focus this year!

 Stewart’s Response: Michael Jordan, MBA, PMP thank you for your comment. That’s a really tough challenge that Entrepreneurs face. What tools, techniques, and/or tactics are you using or exploring to overcome it? Value-based prioritization, delegation, time management best practices, etc.?

Join the discussion. What are your thoughts? What challenges are you currently facing?

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