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How To Ask For Help As A New Entrepreneur

I want to share my learning as a new entrepreneur, shifting from a corporate job to creating and managing a business on my own.

Wow!  Where did all the expertise I had before in a large organization go?

Wow!  This stuff is taking up more… time, resources, headspace, learning curve, effort, labour than I have! or thought it would take!

Wow!  I’m going to give all my accounting and bookkeeping friends big hugs next time I see them. 

There are 2 big thoughts that emerge for me:

Look at what managing a business is for me and identify where I need help

How can I ask for help as a new entrepreneur and what  options I can consider

Look at what managing a business is for me and identify where I need help

To me, it was important to determine where I need help.  As I operate within the business cycle, I begin to notice a few things:


  • Which parts of the business do I enjoy doing?
  • Which parts of the business am I good at?  I already know how to do it.  I can do it efficiently and effectively.  I can optimize this part.
  • Which parts of the business require a learning curve?  I need to learn about it.  I need to learn how to do it.  And more importantly, I am willing to invest traded time from other parts of the business to do this.
  • Which parts of the business are critical?  Must have.  Nice to have.

Download (click here) the working template to follow along if that’s more helpful as I explain it

Here is a simple list that came to mind on the life-cycle of my business that I was operating in. I’ve kept the lens quite simple, recognizing that in complex organizations, there are way more components. But for the budding entrepreneur, there is only so much time and resources available that I narrowed it down the basics. What keeps the lights on for my business? What are the key steps right now?

The evaluation process (example below):

  1. Write down the key tasks you do within your business (how you break it up, is up to you, but big enough that they are grouped by function such as: Marketing, Finance, Business Development, Consumer Management, Operations, Human Resourcing, Strategy)
  2. Pick a criteria important to you to grade against (I picked 2 lens important to me: What am I good at? and What do I enjoy doing? That was all that mattered to me now)
  3. Grade each task against your criteria with a grade
  4. The higher the grade, the more likely I would keep in house and do myself. The lower the grade, the more consideration I would take on alternatives to ask for help.

    Here’s what the data tells you…


    I focused on the lowest numbers.  These are the tasks I’m not very good at and I don’t enjoy doing.  What else can you deduce from just looking at your own evaluation?  That’s up to you to do and decide, but it gives you a starting point about being realistic in where to focus your energies.

    Think about it.  Something that is new, requires learning, I’m not good at, nor do I enjoy doing, why do it?  If you’re saying YES to these things, what are you saying NO to?  What I want to challenge is, let’s reverse this. 

    SAY NO to your low value tasks
    so you can
    SAY YES to the high value ones

    Now think about the next steps once you have decided what NOT to take on yourself is: 

    • Ask friends and other new entrepreneurs – ask them how they managed their financials or did their bookkeeping or what software they are using for consumer management.
    • Google google google – one of the best places to just START searching for information.  I’ll search terms like “lead generation companies in Toronto” or “marketing agency for SMEs in Markham” or “remote office locations in North York” .
    • Join forums and just watch, listen, and learn.  Other entrepreneurs have the same thoughts and challenges.  When someone asks questions of interest, bookmark it and take time to read the other responses and referrals.  There are tonnes of groups on LinkedIn, Facebook, Reddit that are available to the public so long as you have a profile

    How to reach out and really ASK FOR HELP

    For me, I always thought I could TRY it all alone.  The more I tried, the more I realized, it’s taking up too much time and learning and I suck at this!  In the end, my frustration allowed me to just overcome some of the fears, assumptions, and beliefs I had with asking for help and getting creative on really solving this so I could focus my efforts on the parts I wanted to.

    Use your analysis as the basis of your conversation and be specific with examples of where you need help.

    Do some legwork and self research solutions first.  Know what you know and what you don’t know.

    Be curious and not feel in debt.  You’d be surprised how many people love sharing or pointing in some direction.

    Know when to ask for help.  At one point, you just need to engage.  We can’t do it all ourselves.

    You don’t need to do it alone

    For me, being a solo entrepreneur doesn’t mean going at it alone.  You may want to be the only business owner for your business, but legally, that’s on paper if you’ve established the business structure that way.  That doesn’t mean you can’t get real help, whether it’s from outsourcing, collaborations, trading, partners, family, friends, other entrepreneurs, mentors, and experts out there in their field.  That’s why these experts are experts.  That’s why there are automation tools.  That’s why there’s a freelance market.  

    My personal read is that you don’t and shouldn’t bring everything in house.  In fact, you can’t.  Even some large organizations have began to outsource work because they recognize it’s not their strength, someone can do it better and cheaper, and they’d rather invest in core strengths.

    And my biggest learning is:

     I need to invest
    to make these things happen

    Part of my fear was the cost of investments it would be without really knowing my return.  And, I thought… well, how hard could it be?  I can do this.  I can learn this!  Oh, little did I know, my time was being sucked into some of these tasks, I didn’t have room for the things I really wanted to do.  Now I know when people say, take some investments and commit to your business.  It doesn’t have to be a lot, but it has to be some things that I am traditionally uncomfortable with.

    So what did I do?

    I threw out a significant investment to rebuild my consumer funnel (which included new landing pages, a consumer tracking tool, automated lead activities) and lead generation.  This is an area I knew I was not good at, the current strategy wasn’t working, and my way wasn’t generating the results I needed.  One of the perfect tasks to outsource.

    Trust your gut.  Trust your evaluation.  It’ll make part of your journey as an entrepreneur less painful, and more rewarding!

    I know what I’m good at. 

    I know how I want to invest my time. 

    Pick your battles.

    I think a lot

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