Back in March, I went full-time self-employed. Although I prepared things as best I could by getting my finances in order and being on top of my taxes, I’m still surprised at how many challenges I’ve come across.

I know this seems silly, and I’m sure every other self-employed individual or small business owner deals with similar issues, but somehow I was still caught off guard. From chasing down clients for payment to time management, here’s what I’ve struggled with so far by being self-employed.

self-employment woes

Getting paid

When I had a full-time job, I didn’t really mind when clients were taking 60 days to pay, but now that I’m full-time self-employed, not getting paid within 30 days can really wreck my finances.

I’ve got an emergency fund in place, so I’m never at actual risk of going in the red, but if I’m not getting paid on time, that affects my budgeting. I can’t even imagine how small business owners who have employees deal with clients who don’t pay on time.

To be fair, most companies are great, but every so often I need to chase down clients who haven’t paid on time. Almost always, someone forgot to submit the invoice which is why I didn’t get paid.

Getting a loan

This hasn’t affected me personally since my mortgage isn’t currently up for renewal, but I’ve heard from a few friends who are self-employed that have struggled to get a loan from a bank.

It doesn’t matter if they can show that they’ve had consistent income over the last few years or that their business generates additional revenue, lenders have precise rules when it comes to loans.

Basically, if you don’t have a steady job, it can be challenging to get a loan. When my mortgage is up for renewal in a few years, I likely won’t have an issue getting it renewed since my wife’s income will meet the bank’s lending criteria.

Getting disability insurance

I’ve been unable to get disability insurance. My insurance broker is fantastic, but he’s failed to secure me disability insurance for a few reasons.

Insurance companies don’t seem to like the fact that my income may fluctuate. It doesn’t matter that I’ve been able to provide proof of consistent income, they don’t care since there’s a possibility that I may not make that much in the future. Basically, they’re worried that I’ll make a claim in the future and get paid more than I actually make.

Also, I have some health issues that are a red flag for them. Oddly enough, this wasn’t an issue when I got life insurance. My doctor provided proof that my condition is stable and it has no effect on my health. That doesn’t seem to matter to insurers since my doctor can’t prove that I’ll be 100% healthy in 15 years.

Time management

Time management is something that everyone will likely complain about, but it’s really hit me hard as of late.

Since I run my own business, I have to take care of everything on my own. Sure, I outsource a few things and have some excellent people I collaborate with, but I naturally take care of just about everything that relates to my business.

I’ve been taking a lot of meetings recently just to reconnect with clients and to pick up new work which is excellent, but that can be very time-consuming. The good thing is, I think I just need to make a few minor adjustments to get things back on track.

Final thoughts

I know it sounds like I’m complaining, but I love being self-employed. The challenges that have come with it can be difficult and frustrating, but that’s life right?

Self-Employment Woes


  1. GYM on August 21, 2018 at 1:28 PM

    Sorry to read that you’ve been having a hard time getting disability insurance. It’s good that you have your wife to back you up on the steady income front. Do you enjoy doing what you want whenever you please? Like getting a pizza in the middle of your workday? 🙂

    • Barry Choi on August 21, 2018 at 1:42 PM


      Being able to get Domino’s whenever I want is a huge bonus

  2. NZMuse on August 21, 2018 at 3:48 PM

    Ahh yes getting paid! T is now a month into self employment, aside from the cashflow stuff I think the big challenges for him are the solitary nature of the day to day (eventually plans to scale up and bring on other people but that’s way down the track) and the non billable hours (all the stuff that needs to be done at home, admin, finance, etc) which as someone who’s always been paid hourly is a bit of a shift.

    Bummer about the disability insurance – I’m not sure how it works there, is that basically income replacement? Or is more of a lump sum payout?

    • Barry Choi on August 21, 2018 at 5:07 PM


      I usually have meetings twice a week so it keeps the social aspect going. I do agree that not getting paid to do admin stuff e.g. answering emails is a pain.

      Disability insurance is short term income replacement if I can’t work e.g. I break both my arms and can’t type.

  3. Jeff Romansky on August 23, 2018 at 9:18 AM

    Hey Barry!   I always enjoy reading your articles.  As I told you before, I am a big fan of yours as you are an advocate of disability insurance – which is something I specialize in and very passionate about. Thank you for creating the awareness on the importance of insurance.

    I went on my own in January 2015, so I have been where you are now. Time management and learning to deal with fluctuating income were my biggest challenges. For me, being incorporated and paying myself a steady salary has helped with any stress that comes with fluctuating income.   When it comes to time management, I have learned to outsource and developed systems to help automate parts of my business. I quickly learned that I can’t do it all myself.

    Don’t give up on your search for a disability plan. If your main concern is a short term injury – there are definitely options out there for you.  Some companies can at least offer you injury only coverage without any medical or financial underwriting (up to $2,000 of monthly coverage) .  If your needs are higher, you may have access to other plans that only look at your past 6 months of business revenue. Unfortunately, your occupation itself will be a concern for that plan.
    This means you will need your broker to negotiate with underwriting (before submitting an application) to determine if they will insure your occupation or not.  Go back to your broker and ask them to keep looking. 

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